(RS)-1-cyclohexyl-2-propyn-1-ol | 91098-88-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (RS)-1-cyclohexyl-2-propyn-1-ol
• 英文别名: 3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propyne；(3S)-3-(tert-butyldimethyl-siloxy)-3-cyclohexylprop-1-yne；3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-yne；(S)-3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-yne；(3S)-3-(t-Butyldimethylsiloxy)-3-cyclohexylprop-1-yne；3-(t-butyldimethylsilyloxy)-3-cyclohexylprop-1-yne；tert-butyl-(1-cyclohexylprop-2-ynoxy)-dimethylsilane
• CAS: 91098-88-3
• 化学式: C₁₅H₂₈OSi
• 分子量: 252.472
• InChiKey: HQSDNUBPNJEFFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  70-71 °C(Press: 0.5 Torr)
• 密度：
  0.890±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (RS)-1-cyclohexyl-2-propyn-1-ol 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 硫酸 、 三氟化硼乙醚 、 dimsylsodium 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 29.33h， 生成 butanoic acid, 4-[(1S,2S,3R,6S)-2-[(3S)-3-cyclohexyl-3-hydroxy-1-propynyl]-3-hydroxybicyclo[4.2.0]oct-7-ylidene]-(4Z)
  参考文献：
  名称：

  Potent prostacyclin analogs based on the bicyclo[4.2.0]octane ring system

  摘要：

  DOI：

  10.1021/jo00389a038
• 作为产物：
  描述：

  1-cyclohexylprop-2-yn-1-ol 、 叔丁基二甲基氯硅烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以71%的产率得到(RS)-1-cyclohexyl-2-propyn-1-ol
  参考文献：
  名称：

  Potent prostacyclin analogs based on the bicyclo[4.2.0]octane ring system

  摘要：

  DOI：

  10.1021/jo00389a038

文献信息

• <i>tert</i>-Butyldimethylsilyl-Directed Highly Enantioselective Approach to Axially Chiral α-Allenols
  作者：Juntao Ye、Wu Fan、Shengming Ma

  DOI：10.1002/chem.201201948

  日期：2013.1.7

  A highly efficient and enantioselective synthesis of axially chiral α‐allenols was realized in practical yields with 96–99 % ee or de from TBS‐protected propargylic alcohols, aldehydes, and a commercially available, inexpensive, chiral, secondary amine (S)‐α,α‐diphenylprolinol or its enantiomer followed by desilylation. The easily removable TBS group not only acts as a protecting group, but also as

  从TBS保护的炔丙醇，醛和市售的廉价手性仲胺（S）-α中以96-99％ee或de的实际收率实现了轴向手性α-烯醇的高效和对映选择性合成 ，α-二苯基脯氨醇或其对映异构体，然后进行去甲硅烷基化。易于除去的TBS基团不仅充当保护基团，而且还充当可能的空间定向基团，以实现出色的对映选择性并就地防止可能的烯丙基外消旋化。
• OPTICALLY ACTIVE AXIALLY CHIRAL ALPHA-ALLENIC ALCOHOL, SYNTHESIS METHOD AND USE THEREOF
  申请人：SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES

  公开号：US20150105567A1

  公开（公告）日：2015-04-16

  The present invention relates to an optically active axially chiral α-allenic alcohol, a synthetic method and use thereof. A method of preparing a high optically active chiral α-allenic alcohol by using propargyl alcohol, aldehyde and chiral α,α-diphenyl-L-prolinol under the protection of tert-butyldimethylsilyl with a mediator zinc bromide. The axially chiral α-allenic alcohol has the structural formula (I). The method of the present invention has the following advantages: the synthesis route is short, operations are simple, raw materials are readily available, separation and purification are convenient, the substrate has high generality, the total yield is high, and enantioselectivity and diastereoselectivity are high. The high optically active axially chiral α-allenic alcohol synthesized by adopting the method of the present invention can conveniently synthesize 2,5-dihydrofuran compounds having central chirality via complete chirality transfer, and at the same time can further be used to synthesize axially chiral allenic amine and allenic malonate compounds without reacemization.

  本发明涉及一种光学活性轴向手性α-亚烯醇，其合成方法和用途。通过在叔丁基二甲基硅保护下使用丙炔醇、醛和手性α,α-二苯基-L-脯氨醇，在锌溴化物介质的保护下制备高光学活性手性α-亚烯醇的方法。轴向手性α-亚烯醇的结构式为（I）。本发明的方法具有以下优点：合成路线短，操作简单，原料易得，分离和纯化方便，底物通用性高，总收率高，并且对映选择性和对映异构选择性高。采用本发明方法合成的高光学活性轴向手性α-亚烯醇可以通过完全手性转移方便地合成具有中心手性的2,5-二氢呋喃化合物，同时还可以进一步用于合成轴向手性亚烯胺和亚烯丙二酸酯化合物而不发生消旋。
• Novel 8-(lower alkyl)bicyclo[4.2.0]octane derivatives with valuable
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04678805A1

  公开（公告）日：1987-07-07

  Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension, and atherosclerosis are compounds depicted in formulas (1), (2), and (3): ##STR1## wherein: Y is exo-(lower alkyl) or endo-(lower alkyl); n is 2 or 3; R.sub.1 is CH.sub.2 OH, CHO, CO.sub.2 R or CO.sub.2 H; R.sub.2 is hydrogen or methyl; and R.sub.3 is linear or branched alkyl having 5-10 carbon atoms, ##STR2## or --(CH.sub.2).sub.m -phenyl optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen, in which a is 0, 1 or 2; b is 3-7; m is 1 or 2; and R is ##STR3## wherein X is ##STR4## in which each R.sub.4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, and the pharmaceutically acceptable, non-toxic salts and esters thereof.

  有用于治疗心血管疾病如血栓、高血压和动脉粥样硬化的化合物，这些化合物的结构式为(1)、(2)和(3)：##STR1## 其中：Y是外向-(低烷基)或内向-(低烷基)；n为2或3；R.sub.1是CH.sub.2 OH、CHO、CO.sub.2 R或CO.sub.2 H；R.sub.2是氢或甲基；R.sub.3是线性或支链烷基，具有5-10个碳原子，##STR2## 或--(CH.sub.2).sub.m-苯，可选地用低烷基、低烷氧基、三氟甲基或卤素取代，其中a为0、1或2；b为3-7；m为1或2；R为##STR3## 其中X为##STR4## 在其中，每个R.sub.4独立地是氢或具有1-6个碳原子的低烷基，以及其药学上可接受的、无毒的盐和酯。
• Novel [4,2,0]bicyclooctane derivatives with valuable therapeutic
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04608388A1

  公开（公告）日：1986-08-26

  Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension, and atherosclerosis are compounds depicted in formulas (1), (2), and (3): ##STR1## wherein: n is 2 or 3; R.sub.1 is CH.sub.2 OH, CHO, CO.sub.2 R or CO.sub.2 H; R.sub.2 is hydrogen or methyl; and R.sub.3 is linear or branched alkyl having 5-10 carbon atoms, ##STR2## optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen, in which a is 0, 1 or 2; b is 3-7; m is 1 or 2; and R is ##STR3## in which each R.sub.4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, and the pharmaceutically acceptable, non-toxic salts and esters thereof.

  有用于治疗心血管疾病如血栓形成、高血压和动脉粥样硬化的化合物，其中化学式（1）、（2）和（3）所示的化合物为：##STR1## 其中：n为2或3；R.sub.1为CH.sub.2 OH，CHO，CO.sub.2 R或CO.sub.2 H；R.sub.2为氢或甲基；R.sub.3为直链或支链烷基，具有5-10个碳原子，##STR2## 可选地被低碳烷基，低碳氧基，三氟甲基或卤素取代，其中a为0、1或2；b为3-7；m为1或2；R为##STR3## 其中每个R.sub.4独立地为氢或具有1-6个碳原子的低碳烷基，以及其药学上可接受的、无毒的盐和酯。
• Opening of a 1,3-dioxolane by nucleophilic attack at a ketal methylene
  作者：Klaus K. Weinhardt

  DOI：10.1016/s0040-4039(01)90035-8

  日期：——