methyl dl-2-benzyloxy-5-oxo-6-bromo-5,6,7,8-tetrahydro-1-naphthoate | 65860-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl dl-2-benzyloxy-5-oxo-6-bromo-5,6,7,8-tetrahydro-1-naphthoate
• 英文别名: methyl 6-bromo-5-oxo-2-phenylmethoxy-7,8-dihydro-6H-naphthalene-1-carboxylate
• CAS: 65860-12-0
• 化学式: C₁₉H₁₇BrO₄
• 分子量: 389.246
• InChiKey: DPQHHERKPLXSPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl dl-2-benzyloxy-5-oxo-6-bromo-5,6,7,8-tetrahydro-1-naphthoate 生成 methyl dl-2-benzyloxy-5-oxo-6-azido-5,6,7,8-tetrahydro-1-naphthoate
  参考文献：
  名称：

  BACH, N. J.;KORNFELD, E. C.;TITUS, R. D.

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl-2-benzyloxy-5-oxo-5,6,7,8-tetrahydro-1-naphthoate 生成 methyl dl-2-benzyloxy-5-oxo-6-bromo-5,6,7,8-tetrahydro-1-naphthoate
  参考文献：
  名称：

  BACH, N. J.;KORNFELD, E. C.;TITUS, R. D.

  摘要：

  DOI：

文献信息

• Syntheses of 1,2-N-alkylimino-1,2,3,4-tetrahydronaphthalene derivatives and preparation of ring closed analog of salbutamol as a new .BETA.-adrenoceptor agent.
  作者：HIROSADA SUGIHARA、KIYOSHI UKAWA、AKIO MIYAKE、KATSUMI ITOH、YASUSHI SANNO

  DOI：10.1248/cpb.26.394

  日期：——

  A method for preparing 5-substituted 2-tertiary-alkylamino-6-hydroxy-1, 2, 3, 4-tetrahydro-1-naphthalenols was described. The method involves the preparation of 1-alkylamino-2-hydroxy-1, 2, 3, 4-tetrahydronaphthalenes from 2-bromo-1-hydroxy derivatives via 1, 2-epoxides followed by the transposition of 1-alkylamino and 2-hydroxy groups via the ring closure to 1, 2-aziridines. Formation of the epoxides and aziridines and the reaction of epoxides with amines were examined in detail. The ring-opening reaction of epoxides was regioselective and the attacking position of a nucleophile was not affected by the electronic effects of substituents on the benzene ring. Cyclization into aziridine rings was best accomplished by the Wenker method using a sulfur trioxide-triethylamine adduct as the sulfating agent. Using our process, trans-2-tert-butylamino-6-hydroxy-5-hydroxymethyl-1, 2, 3, 4-tetrahydro-1-naphthalenol (70) was synthesized as conformationally fixed analog of salbutamol.

  描述了一种制备5-取代2-叔烷基氨基-6-羟基-1,2,3,4-四氢-1-萘酚的方法。该方法包括由2-溴-1-羟基衍生物通过1, 2-环氧化物制备1-烷基氨基-2-羟基-1,2,3,4-四氢萘，然后将1-烷基氨基和2-羟基转位基团通过闭环形成1, 2-氮丙啶。详细研究了环氧化物和氮丙啶的形成以及环氧化物与胺的反应。环氧化物的开环反应具有区域选择性，亲核试剂的攻击位置不受苯环上取代基的电子效应影响。环化成氮丙啶环最好通过 Wenker 方法使用三氧化硫-三乙胺加合物作为硫酸化剂来完成。使用我们的方法，合成了反式-2-叔丁基氨基-6-羟基-5-羟甲基-1,2,3,4-四氢-1-萘酚 (70)，作为沙丁胺醇的构象固定类似物。
• Improvements in and relating to substituted tetrahydrona phthalenes
  申请人：ELI LILLY AND COMPANY

  公开号：EP0109815A1

  公开（公告）日：1984-05-30

  DI-1-(or 3-) carbamoyl-2-hydroxy-5,6,7,8- tetrahydro- naphthalenes of the formula wherein: one of R and R1 is H and the other is CONH2, R2 and R3 are individually H, methyl, ethyl or n-propyl, and pharmaceutically-acceptable acid addition salts thereof. The compounds are prepared by amidating the 1-(or 3-)ester or carboxhydrizide by reducing the 6-azide, by cleaving the 2-benzyl-oxy group, or by alkylating the 6- amine. These compounds possess a dopamine- like pharmacological activity.

  式中的 DI-1-（或 3-）氨基甲酰基-2-羟基-5,6,7,8-四氢-萘 其中 R 和 R1 中的一个是 H，另一个是 CONH2、 R2 和 R3 分别为 H、甲基、乙基或正丙基，以及 其药学上可接受的酸加成盐。 通过还原 6-叠氮化物、裂解 2-苄氧基或烷基化 6-胺，酰胺化 1-（或 3-）酯或羧肼，可以制备这些化合物。 这些化合物具有类似多巴胺的药理活性。
• BACH, N. J.;KORNFELD, E. C.;TITUS, R. D.
  作者：BACH, N. J.、KORNFELD, E. C.、TITUS, R. D.

  DOI：——

  日期：——
• BACH, N. J.;KORNFELD, E. C.;TITUS, D.
  作者：BACH, N. J.、KORNFELD, E. C.、TITUS, D.

  DOI：——

  日期：——
• SUGIHARA H.; UKAWA K.; KURIKI H.; NISHIKAWA M.; SANNO Y., CHEM. AND PHARM. BULL. <CPBT-AL>, 1977, 25, NO 11, 2988-3002
  作者：SUGIHARA H.、 UKAWA K.、 KURIKI H.、 NISHIKAWA M.、 SANNO Y.

  DOI：——

  日期：——