7-Bromo-heptanoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester | 166403-48-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 7-Bromo-heptanoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 7-bromoheptanoate
• CAS: 166403-48-1
• 化学式: C₃₄H₅₇BrO₂
• 分子量: 577.729
• InChiKey: RIIXLGWHEXVZFZ-DYQRUOQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-Bromo-heptanoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 在 copper(l) iodide 、 sodium azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4'-{[1-(6-cholesteryloxycarbonyl)-1H-1,2,3-triazol-4-ylmethoxy-4-(4-(R,S)-2-methylbutyloxycarbonylphenyl)phenyl]}hexane
  参考文献：
  名称：

  非对称液晶二聚体中三唑环近晶相的合成，表征及分子组织

  摘要：

  通过点击反应合成了含有胆固醇，三唑和联亚苯基的新型非对称液晶二聚体。柔性间隔物长度的增加影响中间相的形成。具有短和中等烷基间隔基的同系物表现出SmA *和SmC *相，而具有最长间隔基的类似物则有利于对映SmA和N *相的形成。XRD研究揭示了SmA *和SmC *相的出现，这些相可能与这些二聚体的单层排列有关。通过比较研究的进一步研究表明，三唑环影响中间相的形成，其中除分子偶极子外，微妙的静电相互作用和范德华力增强了SmC *相。

  DOI：

  10.1016/j.tet.2015.04.036
• 作为产物：
  描述：

  7-溴庚酸 、 胆固醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到7-Bromo-heptanoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  非对称液晶二聚体中三唑环近晶相的合成，表征及分子组织

  摘要：

  通过点击反应合成了含有胆固醇，三唑和联亚苯基的新型非对称液晶二聚体。柔性间隔物长度的增加影响中间相的形成。具有短和中等烷基间隔基的同系物表现出SmA *和SmC *相，而具有最长间隔基的类似物则有利于对映SmA和N *相的形成。XRD研究揭示了SmA *和SmC *相的出现，这些相可能与这些二聚体的单层排列有关。通过比较研究的进一步研究表明，三唑环影响中间相的形成，其中除分子偶极子外，微妙的静电相互作用和范德华力增强了SmC *相。

  DOI：

  10.1016/j.tet.2015.04.036

文献信息

• Photo-responsive liquid crystals derived from azobenzene centered cholesterol-based tetramers
  作者：Monika Gupta、Vaibhav Pal、Santanu Kumar Pal

  DOI：10.1039/c7nj05142e

  日期：——

  Azobenzene centered cholesterol based tetramers showing spherulitic domains and photoresponsive behaviour in solution as well as Langmuir monolayers.

  苯偶氮中心的胆固醇基四聚体在溶液和Langmuir单层中显示出球状结构域和光响应行为。
• Dimesogenic compounds consisting of cholesterol and fluorinated azobenzene moieties: dependence of liquid crystal properties on spacer length and fluorination of the terminal tail
  作者：Woo-Keun Lee、Kyu-Nam Kim、Marie France Achard、Jung-Il Jin

  DOI：10.1039/b516141j

  日期：——

  The liquid crystalline (LC) properties of two series of non-symmetric dimesogenic compounds consisting of cholesterol and ring-fluorinated azobenzene mesogenic moieties interconnected by ω-oxyalkanoyl spacers of varying length are compared; one series (F-AOC-n) has the octyloxy tail attached to the fluorinated azobenzene mesogen unit while the other (F-AOCF-n) has the perfluoroheptylmethyloxy tail. In general, compounds with the fluorinated alkoxy tail exhibited a mesophase over a much wider temperature range than those with the alkoxy tail. On the other hand, the F-AOC-n series exhibited a greater variety of mesophases: TGB (twisted grain boundary), chiral smectic C (SC*), antiphase smectic A (SÃ), cholesteric (N*) and solid state smectic (SX) phases were observed depending on the length of the central spacer, whereas the F-AOCF-n series favored the formation of only the SA phase with the N* phase completely suppressed. Both series showed an odd-even dependence of the isotropization temperature on the spacer length.

  比较了两系列非对称二向色性化合物的液晶性质，这些化合物由胆甾醇和环氟化的偶氮苯介晶基团组成，通过不同长度的ω-氧烷酰间隔基连接；其中一系列（F-AOC-n）在氟化的偶氮苯介晶单元上连接了辛氧基尾，而另一系列（F-AOCF-n）则连接了全氟庚基甲氧基尾。总的来说，具有氟化烷氧基尾的化合物的液晶相温度范围更广，而具有烷氧基尾的化合物的温度范围较窄。另一方面，F-AOC-n系列表现出更丰富的液晶相：根据中心间隔基的长度，观察到了扭结晶界（TGB）、手性层状C（SC*）、反相层状A（SÃ）、胆甾相（N*）和固态层状（SX）相，而F-AOCF-n系列主要形成层状A（SA）相，完全抑制了N*相的形成。两系列化合物均显示出间隔基长度的奇偶依赖性，对均质化温度有影响。
• Observation of helical self-assembly in cyclic triphosphazene-based columnar liquid crystals bearing chiral mesogenic units
  作者：Shruti Rani、Vidhika Punjani、Santosh Prasad Gupta、Madhu Babu Kanakala、C. V. Yelamaggad、Santanu Kumar Pal

  DOI：10.1039/d2tc03847a

  日期：——

  function-integrated smart materials resulting from the spontaneous self-assembly of appropriately chosen functional molecules. Working in this direction, we have synthesized a new series of non-conventional, chiral columnar liquid crystals (Col LCs), where the cyclotriphosphazene core is surrounded by cholesterol-based Schiff base dimeric units. Cholesterol, which is covalently bound to the two-ring Schiff base

  Nowadays, intensive research has focused on the design and synthesis of function-integrated smart materials resulting from the spontaneous self-assembly of appropriately chosen functional molecules. 朝着这个方向努力，我们合成了一系列新的非常规手性柱状液晶 (Col LC)，其中环三磷腈核心被基于胆固醇的席夫碱二聚单元包围。胆固醇，通过以下方式共价结合到双环席夫碱核上一个不同长度和奇偶校验的柔性垫片，已被有预谋地结合起来，以在 Col 流体宏观结构中诱导手性。这些研究使用多种互补技术，清楚地揭示了间隔物的长度而不是奇偶性对由合成化合物的固有 Col 组装产生的 2D 晶格对称性的影响。通过详细的电子密度映射和小角/广角
• Nakamura, Naotake; Hanasaki, Tomonori; Onoi, Hidekazu, Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1993, vol. 225, p. 269 - 278
  作者：Nakamura, Naotake、Hanasaki, Tomonori、Onoi, Hidekazu

  DOI：——

  日期：——
• From smectic to columnar phase of polypedal liquid crystals based on tetrathiafulvalene/1,3-dithiol-2-thione and cholesterol
  作者：Ruibin Hou、Ke-li Zhong、Zhegang Huang、Long Yi Jin、Bingzhu Yin

  DOI：10.1016/j.tet.2010.11.088

  日期：2011.2

  Bipedal 1,3-dithiole-2-thiones attached two cholesteryl through a omega-thioalkanoyloxy spacer of varying length were synthesized. The bipedals were easily transformed to the appropriate tetrapedal tetrathiafulvalene derivatives by self-coupling reaction in net triethyl phosphite. All the synthesized compounds exhibit mesogenic phases in a wide temperature region, no crystallization but vitrifying to form glassy mesogens during cooling from the isotropic melt. The liquid crystals with shorter spacer (n=2-6) exhibited only a smectic A phase and those with the longest spacer (n=7) exhibited only a hexagonal columnar. In these series, the molecular packing depended on the length of spacers. (C) 2010 Elsevier Ltd. All rights reserved.