4-hydroxy-5,5-trimethylene-1-octyne | 69647-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-5,5-trimethylene-1-octyne
• 英文别名: 1-(1-Propylcyclobutyl)but-3-yn-1-ol；4-(1-Propyl-cyclobutyl)-but-1-in-4-ol；5,5-Propano-oct-1-in-4RS-ol
• CAS: 69647-71-8
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: HRXHZRQAZJHFGL-UHFFFAOYSA-N

物化性质

• 沸点：
  261.2±13.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5,5-trimethylene-1-octyne 在 2,6-二甲基吡啶 、 Schwartz's reagent 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.84h， 生成 (E)-1-iodo-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octene
  参考文献：
  名称：

  Development of a highly selective EP2-receptor agonist. Part 1: identification of 16-hydroxy-17,17-trimethylene PGE2 derivatives

  摘要：

  Design and synthesis of an EP2-receptor selective agonist began with the chemical modification of alpha- and omega-chains of butaprost 1a, which exhibits an affinity for the IP-receptor. Two series of prostaglandin (PG) analogues with a 16-hydroxy-17,17-trimethylene moiety as an omega-chain were identified. Among those tested, 4a,b,e,f,h and 6a,b,e,f,h were found to be highly selective EP2-receptor agonists. Structure activity relationships are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00369-8
• 作为产物：
  描述：

  环丁基甲酸 在 lithium aluminium tetrahydride 、 草酰氯 、 magnesium 、 二甲基亚砜 、 三乙胺 、 mercury dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 4-hydroxy-5,5-trimethylene-1-octyne
  参考文献：
  名称：

  Development of a highly selective EP2-receptor agonist. Part 1: identification of 16-hydroxy-17,17-trimethylene PGE2 derivatives

  摘要：

  Design and synthesis of an EP2-receptor selective agonist began with the chemical modification of alpha- and omega-chains of butaprost 1a, which exhibits an affinity for the IP-receptor. Two series of prostaglandin (PG) analogues with a 16-hydroxy-17,17-trimethylene moiety as an omega-chain were identified. Among those tested, 4a,b,e,f,h and 6a,b,e,f,h were found to be highly selective EP2-receptor agonists. Structure activity relationships are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00369-8

文献信息

• Preparation of 15-deoxy-16-hydroxyprostaglandins
  申请人：Miles Laboratories, Inc.

  公开号：US04132738A1

  公开（公告）日：1979-01-02

  Analogues of PGE.sub.1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R.sub.1 is hydrogen; R.sub.2 is hydrogen or together with R.sub.4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R.sub.3 is hydrogen or methyl, or together with R.sub.4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R.sub.4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## SUCH THAT A BICYCLOALKYL OR BICYCLOALKENYL COMPOUND IS FORMED, WHEREIN M AND N ARE INTEGERS HAVING A VALUE FROM 0 TO 3, P IS AN INTEGER HAVING A VALUE FROM 0 TO 4 AND Q IS AN INTEGER HAVING A VALUE OF FROM 1 TO 4 AND WHEREIN THE DOUBLE BOND OF SUCH BICYCLOALKENYL IS IN THE M, N, P, OR Q BRIDGE; R.sub.4 is hydrogen or methyl or together with R.sub.2 or R.sub.3 forms a cycloalkyl or bicycloalkyl or bicycloalkenyl as defined above, or together with R.sub.5 is a methylene chain of 3 to 5 carbon atoms such that a cycloalkyl of 4 to 6 carbon atoms inclusive is formed; R.sub.5 is selected from the group consisting of hydrogen, straight-chain alkyl having from 1 to 3 carbon atoms or together with R.sub.4 forms a cycloalkyl as defined above; and R.sub.6 is hydrogen or straight-chain alkyl having from 1 to 3 carbon atoms are disclosed. Pge.sub.1 ester analogues of the above formula, limited to the structures wherein two of R.sub.2, R.sub.3 R.sub.4 and R.sub.5 form a cycloalkyl, lower alkylated cycloalkyl, bicycloalkyl or bicycloalkenyl are also disclosed. The prostaglandin analogues selectively produce bronchodilation and decrease gastric secretion in vivo. Methods of preparing the analogues and starting materials required in the synthesis of the analogues are also disclosed.

  具有结构式##STR1##的PGE.sub.1的类似物，其中J是R-羟甲亚甲基或S-羟甲亚甲基；R.sub.1是氢；R.sub.2是氢或与R.sub.4一起是2到3个碳原子的亚甲基链，形成包括5到6个碳原子的环烷基；R.sub.3是氢或甲基，或与R.sub.4一起是2到5个碳原子的亚甲基或低烷基化亚甲基链，形成包括4到7个碳原子的环烷基或低烷基化环烷基，或与R.sub.4一起是具有式子的双环烷基或双环烯基基团：##STR2##形成双环烷基或双环烯基化合物，其中M和N是具有值从0到3的整数，P是具有值从0到4的整数，Q是具有值从1到4的整数，且此类双环烯基的双键位于M、N、P或Q桥上；R.sub.4是氢或甲基，或与R.sub.2或R.sub.3一起形成如上定义的环烷基或双环烷基或双环烯基，或与R.sub.5一起是3到5个碳原子的亚甲基链，形成包括4到6个碳原子的环烷基；R.sub.5选自由氢、具有1到3个碳原子的直链烷基或与R.sub.4一起形成如上定义的环烷基；R.sub.6是氢或具有1到3个碳原子的直链烷基。上述结构的Pge.sub.1酯类似物，限于其中两个R.sub.2、R.sub.3、R.sub.4和R.sub.5形成环烷基、低烷基化环烷基、双环烷基或双环烯基的结构也被披露。这些前列腺素类似物在体内选择性地产生支气管扩张并减少胃分泌。还披露了制备这些类似物以及合成这些类似物所需的起始物料的方法。
• Novel Sulfonamides
  申请人：Burk M. Robert

  公开号：US20070043090A1

  公开（公告）日：2007-02-22

  The present invention provides wherein R 1 is selected from the group consisting of C 1 -C 10 alkoxy, OH and NR 4 R 5 ; R 2 is selected from the group consisting of C 1 -C 10 alkyl and (CH 2 ) n OH; R 3 is selected from the group consisting of C 1 -C 10 alkyl, heteroaryl, e.g. thienyl, furanyl and pyridyl, phenyl, mono, -di-, tri-substituted phenyl and heteroaryl; R 4 and R 5 are independently selected from the group consisting of H, C 1 -C 10 alkyl, C 1 -C 10 alkyl hydroxyl; m is 0 or an integer from 1 to 3 and n is an integer of from 1 to 4. These compounds are useful in lowering intraocular pressure and/or treating glaucoma or providing neuroprotection to the eye of a human patient.

  本发明提供其中R1选自C1-C10烷氧基，OH和NR4R5所组成的群；R2选自C1-C10烷基和(CH2)nOH所组成的群；R3选自C1-C10烷基，杂环芳基，如噻吩基，呋喃基和吡啶基，苯基，单取代，双取代，三取代苯基和杂环芳基；R4和R5分别选自H，C1-C10烷基，C1-C10烷基羟基；m为0或从1到3的整数，n为从1到4的整数。这些化合物在降低眼内压和/或治疗青光眼或为人类患者的眼睛提供神经保护方面具有用处。
• Sulfonamides
  申请人：Allergan, Inc.

  公开号：US07314890B2

  公开（公告）日：2008-01-01

  The present invention provides wherein R1 is selected from the group consisting of C1-C10 alkoxy, OH and NR4R5; R2 is selected from the group consisting of C1-C10 alkyl and (CH2)nOH; R3 is selected from the group consisting of C1-C10 alkyl, heteroaryl, e.g. thienyl, furanyl and pyridyl, phenyl, mono, -di-, tri-substituted phenyl and heteroaryl; R4 and R5 are independently selected from the group consisting of H, C1-C10 alkyl, C1-C10 alkyl hydroxyl; m is 0 or an integer from 1 to 3 and n is an integer of from 1 to 4. These compounds are useful in lowering intraocular pressure and/or treating glaucoma or providing neuroprotection to the eye of a human patient.

  本发明提供了一种化合物，其中R1选自C1-C10烷氧基，羟基和NR4R5的群；R2选自C1-C10烷基和(CH2)nOH的群；R3选自C1-C10烷基，杂环芳基，例如噻吩基，呋喃基和吡啶基，苯基，单烷基，双烷基，三烷基苯基和杂环芳基的群；R4和R5独立地选自H，C1-C10烷基，C1-C10烷基羟基；m为0或1至3的整数，n为1至4的整数。这些化合物在降低眼内压和/或治疗青光眼或为人类患者的眼提供神经保护方面有用。
• Novel sulfonamides
  申请人：Burk Robert M.

  公开号：US20080167331A1

  公开（公告）日：2008-07-10

  The present invention provides wherein R 1 is selected from the group consisting of C 1 -C 10 alkoxy, OH and NR 4 R 5 ; R 2 is selected from the group consisting of C 1 -C 10 alkyl and (CH 2 ) n OH; R 3 is selected from the group consisting of C 1 -C 10 alkyl, heteroaryl, e.g. thienyl, furanyl and pyridyl, phenyl, mono, -di-, tri-substituted phenyl and heteroaryl; R 4 and R 5 are independently selected from the group consisting of H, C 1 -C 10 alkyl, C 1 -C 10 alkyl hydroxyl; m is 0 or an integer from 1 to 3 and n is an integer of from 1 to 4. These compounds are useful in lowering intraocular pressure and/or treating glaucoma or providing neuroprotection to the eye of a human patient.

  本发明提供了一种化合物，其中R1选自C1-C10烷氧基，OH和NR4R5组成的群；R2选自C1-C10烷基和(CH2)nOH组成的群；R3选自C1-C10烷基，杂环芳基例如噻吩基、呋喃基和吡啶基，苯基，单、双、三取代苯基和杂环芳基组成的群；R4和R5分别选自H，C1-C10烷基和C1-C10烷基羟基；m为0或1到3的整数，n为1到4的整数。这些化合物可用于降低眼内压和/或治疗青光眼或提供对人类患者眼睛的神经保护。
• Omega-cycloalkyl-prostaglandin E2 derivatives
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0860430B1

  公开（公告）日：2002-06-12