10,15-二氢-2,3,7,8,12,13-六甲氧基-5H-三苯并[a,d,g]环壬烯 | 1180-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 10,15-二氢-2,3,7,8,12,13-六甲氧基-5H-三苯并[a,d,g]环壬烯
• 中文别名: 环三藜芦烯
• 英文名称: cyclotriveratrylene
• 英文别名: Cyclotriveratrylen；CTV；2,3,7,8,12,13-Hexamethoxy-5,10,15-trihydro-tribenzocyclononen；2,3,7,8,12,13-hexamethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene；5,6,12,13,19,20-hexamethoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene
• CAS: 1180-60-5
• 化学式: C₂₇H₃₀O₆
• 分子量: 450.532
• InChiKey: YECHEDVCXXVLIY-UHFFFAOYSA-N

物化性质

• 熔点：
  222-228 °C
• 沸点：
  518.6°C (rough estimate)
• 密度：
  1.1183 (rough estimate)
• 碰撞截面：
  213.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2909309090

SDS

Name:	Cyclotriveratrylene 93% (TLC) Material Safety Data Sheet
Synonym:
CAS:	1180-60-5

Section 1 - Chemical Product MSDS Name:Cyclotriveratrylene 93% (TLC) Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1180-60-5	Cyclotriveratrylene	93 %	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1180-60-5: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 224.00 - 226.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C27H30O6
Molecular Weight: 450.52

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1180-60-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Cyclotriveratrylene - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1180-60-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1180-60-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1180-60-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  10,15-二氢-2,3,7,8,12,13-六甲氧基-5H-三苯并[a,d,g]环壬烯 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到六苯酚
  参考文献：
  名称：

  帽状分子超分子螺旋组织中手性自排序构建的同手性柱

  摘要：

  被手性、外消旋或非手性外围烷基链取代的树枝状环三戊四烯 (CTV) 冠库，包括对映纯的 R 和 S 支链烷基、“混合外消旋”、“合成外消旋”、正辛基和正十二烷基被合成。在疏溶剂溶剂和散装中，它们在螺旋柱中自组装。它们的溶液和体积形状持久的超分子结构由溶液和薄膜中的圆二色性 (CD) 和紫外线、薄膜中的微点 CD、差示扫描量热法与纤维 X 射线衍射相结合、计算机模拟和分子模型。在解决方案中，通过协同机制自组装从对映体纯 CTV 生成单手柱，从外消旋混合、外消旋合成、R 和 S 的其他组合，甚至从非手性化合物生成右旋和左旋列的混合物。在本体状态下，所有超分子柱形成 3D 六方晶相 Φ(h)(k)（P6₃ 对称性），只能从单手柱和柱状六方 2D 液晶 Φ(h) 中获得。最高阶的 Φ(h)(k) 由对映纯单手柱组成，这些柱是略微扭曲的 12 倍三螺旋。“帽子形”树枝状 CTV 组装在弯曲分支的松树

  DOI：

  10.1021/ja5035107
• 作为产物：
  描述：

  3,4-二甲氧基苄氯 在 三氯化铝 、 硫酸 作用下， 生成 10,15-二氢-2,3,7,8,12,13-六甲氧基-5H-三苯并[a,d,g]环壬烯
  参考文献：
  名称：

  Oliverio; Casinovi, Annali di Chimica, 1952, vol. 42, p. 168,175

  摘要：

  DOI：

文献信息

• Supramolecular Scaffolds and Methods of Making the Same
  申请人：Becker Daniel P.

  公开号：US20100041880A1

  公开（公告）日：2010-02-18

  Tribenzo-1,4,7-triazacyclononane and derivatives thereof having a formula (I) are disclosed. Methods of making tribenzo-1,4,7-triazacyclononane and related compounds also are disclosed.

  Tribenzo-1,4,7-triazacyclononane及其衍生物的化学式（I）已被披露。同时也披露了制备Tribenzo-1,4,7-triazacyclononane和相关化合物的方法。
• Lewis acid-catalyzed synthesis of dodecamethoxycalix[4]arene from 1,3,5-trimethoxybenzene and its conformational behavior and host–guest property
  作者：Tomoki Ogoshi、Keisuke Kitajima、Kenji Umeda、Sachi Hiramitsu、Suguru Kanai、Shuhei Fujinami、Tada-aki Yamagishi、Yoshiaki Nakamoto

  DOI：10.1016/j.tet.2009.10.059

  日期：2009.12

  Lewis acid-catalyzed condensation of 1,2- and 1,3-dimethoxybenzenes with paraformaldehyde afforded an ortho-bridged cyclic trimer (1) and a meta-bridged cyclic tetramer (2), respectively. Furthermore, condensation of 1,3,5-trimethoxybenzene with paraformaldehyde in the presence of Lewis acid catalyst successfully rendered the first dodecamethoxy-substituted calix[4]arene (3) with high yield. From X-ray

  路易斯酸催化的1,2-和1,3-二甲氧基苯与低聚甲醛的缩合分别得到邻桥式环状三聚体（1）和间桥式环状四聚体（2）。此外，在路易斯酸催化剂的存在下，1,3,5-三甲氧基苯与低聚甲醛的缩合成功地获得了高产率的第一个十二甲氧基取代的杯[4]芳烃（3）。通过X射线晶体学，发现3形成了部分锥体构象。通过可变温度1研究溶液中3的构象行为1 H NMR测量。固态观察到的部分锥体结构在低温下保留在溶液中。此外，由于在NMR时间尺度上3的构象交换缓慢，因此发现了双峰构象交换。通过UV-Vis测量检查了具有电子接受性客体四氰基乙烯（TCNE）的3的主体-客体性质，与3 -TCNE络合物缔合的能力是2 -TCNE络合物的三倍。该观察结果是由于与相似的2相比，3具有更好的给电子性能和缓慢的构象交换。
• An electron-transfer induced conformational transformation: from non-cofacial “sofa” to cofacial “boat” in cyclotetraveratrylene (CTTV) and formation of charge transfer complexes
  作者：Denan Wang、Maxim V. Ivanov、Saber Mirzaei、Sergey V. Lindeman、Rajendra Rathore

  DOI：10.1039/c8ob01118d

  日期：——

  undergoes oxidation-induced folding, consistent with interconversion from a non-cofacial “sofa” conformation to a cofacial “boat” conformer. It is found that the non-cofacial “sofa” conformer of CTTV forms stable electron donor–acceptor complexes with chloranil and DDQ. Electron-transfer induced conformational transformation in CTTV provides a framework for the rational design of novel organic functional

  经历蛤状机电致动的电活性多色性组件代表了一类重要的有机功能材料。在这里，我们表明，容易获得的环四碳杂戊二烯（CTTV）经历了氧化诱导的折叠，与从非界面“沙发”构象到界面“船形”构象的相互转化一致。已经发现，CTTV的非界面“沙发”构象异构体与氯苯胺和DDQ形成稳定的电子供体-受体复合物。CTTV中电子转移诱导的构象转化为新型有机功能分子的合理设计提供了框架。
• Molecular Structure of Helical Supramolecular Dendrimers
  作者：Mihai Peterca、Virgil Percec、Mohammad R. Imam、Pawaret Leowanawat、Kentaro Morimitsu、Paul A. Heiney

  DOI：10.1021/ja806524m

  日期：2008.11.5

  The molecular structure of helical supramolecular dendrimers generated from self-assembling dendrons and dendrimers and from self-organizable dendronized polymers was elucidated for the first time by the simulation of the X-ray diffraction patterns of their oriented fibers. These simulations were based on helical diffraction theory applied to simplified atomic helical models, followed by Cerius2 calculations

  通过模拟定向纤维的 X 射线衍射图，首次阐明了由自组装树枝状聚合物和树枝状聚合物以及自组织树枝状聚合物产生的螺旋超分子树枝状聚合物的分子结构。这些模拟基于应用于简化原子螺旋模型的螺旋衍射理论，然后是基于其完整分子螺旋结构的 Cerius2 计算。筛选了数百个样品，直到包含 14 个超分子树枝状聚合物和树枝状聚合物的库在其定向纤维的 X 射线衍射图中提供了足够数量的螺旋特征。这种技术组合提供了单 9(2) 和 -11(3) 螺旋、三重 6(1)、-8(1)、-9(1) 和 -12(1) 螺旋的示例，以及由冠状树枝状大分子、空心和非空心超分子冠状树枝状大分子、空心和非空心超分子盘状树枝状大分子以及空心和非空心超分子和大分子螺旋状结构组装而成的八角 32(1) 螺旋。这里阐述的用于确定分子螺旋结构的方法是从结构生物学领域移植过来的，将适用于其他类别的合成螺旋组件。螺旋超分子组件的分子结构的确定有
• Tautomeric equilibria of 2- and 4-thiouracil in gas phase and in solvent: A density functional study
  作者：T. Marino、N. Russo、E. Sicilia、M. Toscano

  DOI：10.1002/1097-461x(2001)82:1<44::aid-qua1020>3.0.co;2-6

  日期：——

  self-consistent reaction field approach by the polarizable continuum model. All calculations indicate that the most stable tautomer for both species, in the gas phase as well as in solution, has the oxo-thione form, in full agreement with the previous ab initio and experimental studies. The tautomeric stability orders obtained in the aqueous solution are sensibly different from that in the gas phase. At B3LYP/6-311++G(d

  气相和水溶液中 2- 和 4-硫尿嘧啶的五种有利互变异构体的相对稳定性通过密度泛函理论采用 Becke、Lee、Yang 和 Parr (B3LYP) 交换相关势和三个 6- 31G(d,p)、6-311++G(d,p) 和三 zeta 价 (TZVP) 基组。还计算了零点振动校正。通过可极化连续介质模型在自洽反应场方法的框架内研究了本体溶剂效应。所有计算表明，两种物质在气相和溶液中最稳定的互变异构体都具有氧代硫酮形式，这与之前的从头计算和实验研究完全一致。在水溶液中获得的互变异构稳定性顺序明显不同于在气相中的互变异构稳定性顺序。在 B3LYP/6-311++G(d, p) 在气相中，2-和 4-硫尿嘧啶互变异构体的稳定性顺序分别为：S2U1>S2U2>S2U4>S2U5>S2U3 和 S4U1>S4U2>S4U3>S4U4>S4U5。水相中相应的趋势是S2U1>S2U3>S2U2>S2U