(1R,2R,6S,8R)-2,9,9-三甲基-4-乙烯基-3,5-二氧杂-4-硼杂三环[6.1.1.02,6]癸烷 | 132488-71-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (1R,2R,6S,8R)-2,9,9-三甲基-4-乙烯基-3,5-二氧杂-4-硼杂三环[6.1.1.02,6]癸烷
• 英文名称: (+)-Vinylboronic acid pinanediol ester
• 英文别名: (1R,2R,6S,8R)-4-ethenyl-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• CAS: 132488-71-2
• 化学式: C₁₂H₁₉BO₂
• 分子量: 206.093
• InChiKey: POAOFRAFKLHZGL-MWGHHZFTSA-N

物化性质

• 密度：
  1.002 g/mL at 25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (+)-Vinylboronic acid pinanediol ester
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: (+)-Vinylboronic acid pinanediol ester
CAS number: 132488-71-2

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C12H19BO2
Molecular weight: 206.1

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸4-联苯基酯 、 (1R,2R,6S,8R)-2,9,9-三甲基-4-乙烯基-3,5-二氧杂-4-硼杂三环[6.1.1.02,6]癸烷 在 2,2,6,6-四甲基哌啶 、 lithium trifluoromethanesulfonate 、 C₃₈H₄₄F₆N₃P₂Pd⁽¹⁺⁾*CH₃O₃S^(1-) 作用下， 以 氟苯 为溶剂， 以50 %的产率得到(3aS,7aR)-3a,5,5-trimethyl-2-(1-([1,1'-biphenyl]-4-yl)vinyl)hexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole
  参考文献：
  名称：

  通过 Pd 催化 Mizoroki-Heck 反应区域选择性合成 α-乙烯基硼酸酯

  摘要：

  我们报道了通过芳基三氟甲磺酸酯和乙烯基硼酸酯之间的区域选择性 Mizoroki-Heck 反应，钯催化合成 α-乙烯基硼酸酯。这种选择性是通过使用 1,5-二氮杂-3,7-二磷环辛烷 (P 2 N 2 ) 配体来实现的，从而最大限度地减少了更常见的（线性）β-产物的形成。碱、溶剂和水的存在的选择对于控制这一结果至关重要，有机碱、非极性溶剂和无水条件有利于 Heck 产物并抑制竞争性的 Suzuki−Miyaura 偶联产物。

  DOI：

  10.1021/acs.orglett.4c02866
• 作为产物：
  描述：

  dichlorovinylborane 、 (1R,2R,3S,5R)-(-)-2,3-蒎烷二醇 在 4-乙烯基吡啶 、 吩噻嗪 作用下， 以 正戊烷 为溶剂， 以57%的产率得到(1R,2R,6S,8R)-2,9,9-三甲基-4-乙烯基-3,5-二氧杂-4-硼杂三环[6.1.1.02,6]癸烷
  参考文献：
  名称：

  光学活性乙烯基硼酸酯

  摘要：

  描述了以（-）-2,3- ane二醇（5）或（+）-酒石酸二乙酯（7）和二氯乙烯基硼烷（4a），乙烯基硼酸（4c）和乙烯基硼酸二丁酯（4d）开头的光学活性乙烯基硼酸酯的对比合成。提出了一种新的合成二卤环戊基硼烷4a，4b的方法。

  DOI：

  10.1016/0022-328x(90)87002-u

文献信息

• Simple, Stable, and Versatile Double-Allylation Reagents for the Stereoselective Preparation of Skeletally Diverse Compounds
  作者：Feng Peng、Dennis G. Hall

  DOI：10.1021/ja068985t

  日期：2007.3.1

  A new and efficient class of double-allylation reagents, α-trimethylsilylmethyl allylboronate 1 and the crotylboronates 12, is reported. These stable bimetallic reagents are prepared easily in enantiomerically pure form and add under BF3 catalysis onto a wide range of aldehydes to afford a direct access to hydroxyl-functionalized allylic silanes in very high E/Z selectivity and excellent enantioselectivity

  报道了一类新型有效的双烯丙基化试剂，α-三甲基甲硅烷基甲基烯丙基硼酸酯 1 和巴豆基硼酸酯 12。这些稳定的双金属试剂很容易以对映体纯形式制备，并在 BF3 催化下添加到各种醛上，以非常高的 E/Z 选择性和出色的对映选择性（高达 98% ee）直接获得羟基官能化的烯丙基硅烷. 有用的羟基官能化烯丙基硅烷中间体可用于各种化合物类别的化学发散合成，例如无环丙酸酯单元、多取代呋喃、乙烯基环丙烷和更大的碳环。
• Optisch aktive vinylboronate
  作者：Ibrahim Mikhail、Dieter Kaufmann

  DOI：10.1016/0022-328x(90)87002-u

  日期：1990.11

  The comparative synthesis of optical active vinylboronates starting with (−)-2,3-pinanediol (5) or (+)-diethyltartrate (7) and dichlorovinylborane (4a), vinylboronic acid (4c), and dibutyl vinylboronate (4d) is described. A new method for the synthesis of dihalovinylboranes 4a, 4b is presented.

  描述了以（-）-2,3- ane二醇（5）或（+）-酒石酸二乙酯（7）和二氯乙烯基硼烷（4a），乙烯基硼酸（4c）和乙烯基硼酸二丁酯（4d）开头的光学活性乙烯基硼酸酯的对比合成。提出了一种新的合成二卤环戊基硼烷4a，4b的方法。