(1E)-(3S)-3-tert-butyldimethylsilyloxy-3-cyclohexyl-1-iodo-1-propene | 82476-95-7

• 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: (1E)-(3S)-3-tert-butyldimethylsilyloxy-3-cyclohexyl-1-iodo-1-propene
• 英文别名: (1E, 3S)-1-iodo-3-(tert-butyldimethylsiloxy)-3-cyclohexyl-1-propene；(1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-3-cyclohexyl-1-propene；(E)-(3S)-t-butyldimethylsilyloxy-3-cyclohexyl-1-iodo-1-propene；tert-butyl-[(E,1S)-1-cyclohexyl-3-iodoprop-2-enoxy]-dimethylsilane
• CAS: 82476-95-7
• 化学式: C₁₅H₂₉IOSi
• 分子量: 380.385
• InChiKey: LGULZQHLELVLEG-GCZGRYASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  18
• 可旋转键数：
  5
• 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：

  (1E)-(3S)-3-tert-butyldimethylsilyloxy-3-cyclohexyl-1-iodo-1-propene 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 methyl (5Z,12E)-(14S)-14-tert-butyldimethylsilyloxy-14-cyclohexyl-9-oxo-5,12-tetradecadienoate
  参考文献：
  名称：

  Synthesis of new secoprostaglandins as inducers of platelet aggregation.

  摘要：

  合成了两系列的8-乙酰基-12-羟基烯二烯酸和14-羟基-9-氧烯二烯酸，这些化合物可以视为11, 12-和8, 12-秒前列腺素E2，并评估了它们对血小板功能的生物活性。每个系列的关键成员，11, 12-和8, 12-秒-11-去羟基前列腺素E2，被发现能够诱导血小板聚集。该效应被前处理的血小板富血浆与前列腺素I2组合抑制，但并未被吲哚美辛抑制。

  DOI：

  10.1248/cpb.30.51
• 作为产物：
  描述：

  3-cyclohexyl-3RS-hydroxy-1-iodoprop-1E-ene 生成 (1E)-(3S)-3-tert-butyldimethylsilyloxy-3-cyclohexyl-1-iodo-1-propene
  参考文献：
  名称：

  Synthesis of 7-thiaprostaglandin E1 congeners: Potent inhibitors of platelet aggregation.

  摘要：

  合成了一系列新型的7-硫前列腺素E1衍生物和同系物，采用一步法的三组分耦合过程，该过程涉及向(R)-4-叔丁基二甲基硅氧基-2-环戊烯酮引入α侧链（硫醇）和β侧链（有机铜试剂）。还通过酶法或化学方法制备了几种7-硫前列腺素E1的酸衍生物。这些产物的立体化学基于对手性保护的环戊烯酮和手性ω侧链的结果进行分配。发现某些7-硫前列腺素E1同系物的血小板聚集抑制活性比PGE1更强。文中讨论了这些同系物的结构-活性关系。

  DOI：

  10.1248/cpb.33.2359

文献信息

• Prostaglandin derivatives
  申请人：Sato Fumie

  公开号：US20060270740A1

  公开（公告）日：2006-11-30

  A prostaglandin derivative represented by the formula (wherein X is a halogen atom; Y is ethylene group, vinylene group or ethylylene group; Z is a group represented by —(CH 2 ) m , —O(CH 2 ) n — or —S(O) p —(CH 2 ) n — (m is an integer of 0 to 3; n is an integer of 0 to 2; and p is an integer of 0 to 2); R 1 is a hydrogen atom, a C 1-5 alkyl group or a substituted C 1-5 alkyl group; R 2 is a C 3-10 cycloalkyl group, a C 3-10 cycloalkyl group substituted by C 1-4 alkyl group or C 4-15 cycloalkylalkyl group; and R 3 is a hydrogen atom, a halogen atom or a C 1-5 alkyl group or a substituted C 1-5 alkyl group), a pharmaceutically acceptable salt thereof or a hydrate thereof which has an excellent antagonism to prostaglandin DP receptor and, therefore, is useful against diseases such as allergic rhinitis, nasal obstruction, asthma, allergic conjunctivitis, systemic mastocytosis and disorder of systemic mast cell activation.

  一种前列腺素衍生物，其化学式为：其中X为卤素原子；Y为乙烯基，乙烯基或乙基基；Z为由-(CH2)m，-O( )n-或-S(O)p-( )n-表示的基团（其中m为0至3的整数；n为0至2的整数；p为0至2的整数）；R1为氢原子，C1-5烷基或取代的C1-5烷基；R2为C3-10环烷基，C3-10环烷基被C1-4烷基或C4-15环烷基烷基取代；R3为氢原子，卤素原子或C1-5烷基或取代的C1-5烷基，其药物可接受的盐或水合物对前列腺素DP受体具有优异的拮抗作用，因此对过敏性鼻炎，鼻塞，哮喘，过敏性结膜炎，系统性肥大细胞病和系统性肥大细胞激活障碍等疾病有用。
• Design and synthesis of a selective EP4-Receptor agonist. Part 1: discovery of 3,7-DithiaPGE1 derivatives and identification of Their ω chains
  作者：Toru Maruyama、Masaki Asada、Tai Shiraishi、Hiromu Egashira、Hideyuki Yoshida、Takayuki Maruyama、Shuichi Ohuchida、Hisao Nakai、Kigen Kondo、Masaaki Toda

  DOI：10.1016/s0968-0896(01)00351-0

  日期：2002.4

  Improvement of EP4-receptor selectivity and the agonist activity by introduction of heteroatoms into the a chain of PGE(1) was investigated. Among the compounds tested, 3,7-dithiaPGE(1) 4a exhibited good EP4-receptor selectivity and agonist activity. Further modification of the omega chain of 3,7-dithiaPGE(1) was performed to improve EP4-receptor selectivity and agonist activity. Of the compounds produced, 16-phenyl-omega-tetranor-3.7-dithiaPGE(1) 4p possessing moderate EP4-receptor selectivity and agonist activity. was identified as a new chemical lead for further optimization by modification of the aromatic moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.
• EP1598335
  申请人：——

  公开号：——

  公开（公告）日：——
• A new efficient synthesis of the biologically potent PGD2-analogue ZK118182
  作者：Sentaro Okamoto、Satoshi Katayama、Naoya Ono、Fumie Sato

  DOI：10.1016/s0957-4166(00)86051-6

  日期：1992.12

  A highly stereoselective and practical synthetic method for ZK118182, which is chemically and metabolically stable and a biologically potent PGD2-analogue developed by Schering AG, is reported.
• TANAKA, TOSIO;YU, KEHN;OBA, TAKEHO;OKAMURA, NORIAKI;VATANABEH, KEHNDZO;SA+
  作者：TANAKA, TOSIO、YU, KEHN、OBA, TAKEHO、OKAMURA, NORIAKI、VATANABEH, KEHNDZO、SA+

  DOI：——

  日期：——