(S)-1-cyclohexyl-2-propyn-1-ol | 105803-39-2

• 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: (S)-1-cyclohexyl-2-propyn-1-ol
• 英文别名: (S)-3-<(tert-Butyldimethylsilyl)oxy>-3-cyclohexyl-1-propyne；(S)-3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-yne；(3S)-3-(t-Butyldimethylsiloxy)-3-cyclohexylprop-1-yne；(3S)-3-(tert-butyldimethyl-siloxy)-3-cyclohexylprop-1-yne；(S)-3-t-butyldimethylsilyloxy-3-cyclohexyl-1-propyne；(3S)-3-(tert-Butyldimethylsiloxy)-3-cyclohexylprop-1-yne；tert-butyl-[(1S)-1-cyclohexylprop-2-ynoxy]-dimethylsilane
• CAS: 105803-39-2
• 化学式: C₁₅H₂₈OSi
• 分子量: 252.472
• InChiKey: HQSDNUBPNJEFFQ-CQSZACIVSA-N

物化性质

• 沸点：
  279.5±13.0 °C(Predicted)
• 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：

  (S)-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 在 chromium(VI) oxide 、 sodium hydroxide 、 (S)-alpine borane 、 硫酸 、 双氧水 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 35.0h， 生成 (S)-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

• Process and intermediates for the synthesis of the enantiomers of bicyclo(4.2.0)oct-2-en-7-one and derivatives and for the synthesis of bicyclo(4.2.0)octane derivatives
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0257610A3

  公开（公告）日：1989-05-24

  The enantiomers of formulas are prepared in a sequence starting from the racemic compound of formulawherein X is hydrogen or bromo when Y is bromo, or X is chloro when Y is chloro.The key step of this process involves a microbial reduction of the compound of formula (3) to give a ketone and an alcohol of high enantiomeric purity. The compounds of formulas (1) and (2) are intermediates for the preparation of certain bicyclo[4.2.0]octane derivatives.

  这些公式的对映异构体是从公式的消旋化合物开始的顺序制备的，其中X为氢或溴，Y为溴时，或者X为氯，Y为氯时。这个过程的关键步骤涉及将公式（3）的化合物进行微生物还原，得到高对映纯度的酮和醇。公式（1）和（2）的化合物是制备某些双环[4.2.0]辛烷衍生物的中间体。
• Novel 6-alkyl and 6.8-dialkylbicyclo(4.2.0)octane derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04983627A1

  公开（公告）日：1991-01-08

  Compounds useful in treating or preventing gastrointestinal ulcers and in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, trans --CH.dbd.CHCH.sub.2 -- or --CH.sub.2 CH.sub.2 --; X is lower alkyl of 1-6 carbon atoms; Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl); n is an integer from 2-4; R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z); R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is trans --CH.dbd.CHCH.sub.2 --; and R.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen. in which: a is an integer of 0, 1 or 2; b is an integer of 3-7; m is an integer of 0, 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, or a pharmaceutically acceptable, non-toxic salt or ester thereof.

  这些化合物适用于治疗或预防胃溃疡，以及治疗心血管疾病，如血栓形成、高血压和动脉粥样硬化，其化学结构如下：##STR1## 其中：A是--C.tbd.C--，trans--HC.dbd.CH--，trans--CH.dbd.CHCH.sub.2--或--CH.sub.2CH.sub.2--；X是1-6个碳原子的低碳基；Y是氢，外-(低碳基)或内-(低碳基)；n是2-4的整数；R.sub.1是--CH.sub.2OH，--CHO，--CO.sub.2R或--CO.sub.2H，R.sub.1(CH.sub.2).sub.nCH.dbd.部分形成的烯烃为(E)或(Z)；R.sub.2是氢或甲基，或当A为trans--CH.dbd.CHCH.sub.2--时可选--CH.dbd.CH.sub.2；R.sub.3是线性或支链烷基，烯基或炔基，具有5-10个碳原子，##STR2## --(CH.sub.2).sub.m-苯基或CH.sub.2O-苯基；其中每个苯基可以选择地用低碳基，低烷氧基，三氟甲基或卤素取代。其中：a是0、1或2的整数；b是3-7的整数；m是0、1或2的整数；R是##STR3## 其中X'是##STR4## 在此，每个R.sub.4独立地是氢或具有1-6个碳原子的低烷基，或其药用可接受的、无毒的盐或酯。
• Prostaglandin derivatives
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：US05545666A1

  公开（公告）日：1996-08-13

  A prostaglandin derivative represented by formula ##STR1## wherein R.sup.1 represents a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, and R.sup.2 represents a cyclohexyl group or a cyclopentylmethyl group. This compound has physiological activities such as platelet aggregation-inhibiting action, renal blood vessel and coronary blood vessel-dilating actions and the like, and is useful for treatment of renal failure and diseases of circulatory organs.

  一种以公式##STR1##表示的前列腺素衍生物，其中R.sup.1代表氢原子或C.sub.1 -C.sub.6烷基，R.sup.2代表环己基或环戊基甲基基团。该化合物具有生理活性，如抑制血小板聚集作用、扩张肾脏血管和冠状动脉血管等，对治疗肾功能衰竭和循环器官疾病有用。
• Prostagladin derivatives
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：US06329539B1

  公开（公告）日：2001-12-11

  A prostaglandin derivative represented by the formula: wherein X is a halogen atom, n is an integer of 1 to 5, R1 is a C3-10 cycloalkyl group, a C3-10 cycloalkyl group substituted with C1-4 alkyl group(s), a C4-13 cycloalkylalkyl group, a C5-10 alkyl group, a C5-10 alkenyl group, a C5-10 alkynyl group or a bridged cyclic hydrocarbon group, and R2 is a hydrogen atom, a C1-10 alkyl group or a C3-10 cycloalkyl group, or a pharmaceutically acceptable salt thereof.

  一种前列腺素衍生物，化学式为：其中X是卤素原子，n为1至5的整数，R1是C3-10环烷基、一个被C1-4烷基取代的C3-10环烷基、C4-13环烷基烷基、C5-10烷基、C5-10烯基、C5-10炔基或桥环烃基，R2是氢原子、C1-10烷基或C3-10环烷基，或其药学上可接受的盐。
• Novel substituted (4.2.0)bicyclooctane derivatives with valuable
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04735966A1

  公开（公告）日：1988-04-05

  Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, --CH.sub.2 CH.sub.2 -- or --CH.dbd.CHCH.sub.2 --; X is lower alkoxy, hydroxy, or (2,2,2)-trifluoroethoxy; Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl); is an integer of 2-4; R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z); R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is --CH.dbd.CHCH.sub.2 --; and R.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen; in which: a is an integer of 0, 1 or 2; b is an integer of 3-7; m is an integer of 0, 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.

  该公式描述了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，其化学式为(1)、(2)和(3)： ##STR1## 其中：A为--C.tbd.C--，顺式--HC.dbd.CH--，--CH.sub.2 CH.sub.2 --或--CH.dbd.CHCH.sub.2 --；X为低级烷氧基，羟基或(2,2,2)-三氟乙氧基；Y为氢，外向式(低级烷基)或内向式(低级烷基)；为2-4的整数；R.sub.1为--CH.sub.2 OH，--CHO，--CO.sub.2 R或--CO.sub.2 H，R.sub.1(CH.sub.2).sub.n CH.dbd.基团形成的烯烃为(E)或(Z)；R.sub.2为氢或甲基，当A为--CH.dbd.CHCH.sub.2 --时，可选择性地为--CH.dbd.CH.sub.2；R.sub.3为线性或支链烷基、烯基或炔基，具有5-10个碳原子， ##STR2## --(CH.sub.2).sub.m-苯基或CH.sub.2 O-苯基；其中每个苯基可以选择性地用低级烷基、低级烷氧基、三氟甲基或卤素取代；其中：a为0、1或2的整数；b为3-7的整数；m为0、1或2的整数；R为 ##STR3## 其中x为 ##STR4## 其中每个R.sub.4独立地为氢或具有1-6个碳原子的低级烷基，以及其药学上可接受的、非毒性的盐和酯。