(3R,4R)-2-methylene-3-[(1E,3S)-3-(tert-butyldimethylsiloxy)-3-cyclohexyl-1-propenyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one | 146382-61-8

• 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: (3R,4R)-2-methylene-3-[(1E,3S)-3-(tert-butyldimethylsiloxy)-3-cyclohexyl-1-propenyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one
• 英文别名: (3R, 4R)-2-methylene-3-[(1E,3S)-3-(tert-butyldimethylsiloxy)-3-cyclohexyl-1-propenyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one；(3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-3-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxy-3-cyclohexylprop-1-enyl]-2-methylidenecyclopentan-1-one
• CAS: 146382-61-8
• 化学式: C₂₇H₅₀O₃Si₂
• 分子量: 478.863
• InChiKey: BJKWJVNZMRYWQJ-TXTKJOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.05
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-2-methylene-3-[(1E,3S)-3-(tert-butyldimethylsiloxy)-3-cyclohexyl-1-propenyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one 在 叔丁基锂 、 4-甲基苯磺酸吡啶 、 L-Selectride 、 lithium,azanidylidenemethylidenecopper,2H-thiophen-2-ide 作用下， 以 四氢呋喃 、 乙醚 、 异丙醇 为溶剂， 反应 21.5h， 生成
  参考文献：
  名称：

  A new efficient synthesis of the biologically potent PGD2-analogue ZK118182

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)86051-6
• 作为产物：
  描述：

  2-((diethylamino)methyl)-4-tert-butyldimethylsiloxy-2-cyclopentenone 、 (1E)-(3S)-3-tert-butyldimethylsilyloxy-3-cyclohexyl-1-iodo-1-propene 在 叔丁基锂 、 lithium,azanidylidenemethylidenecopper,2H-thiophen-2-ide 作用下， 生成 (3R,4R)-2-methylene-3-[(1E,3S)-3-(tert-butyldimethylsiloxy)-3-cyclohexyl-1-propenyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one
  参考文献：
  名称：

  A new efficient synthesis of the biologically potent PGD2-analogue ZK118182

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)86051-6

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(CH2)n-或-S(O)p-(CH2)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。
• 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.