(1S,4R)-4-(Methylamino)cycloheptanol | 217438-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4R)-4-(Methylamino)cycloheptanol
• 英文别名: (1S,4R)-4-(methylamino)cycloheptan-1-ol
• CAS: 217438-68-1
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: HPVMOISALWFVGM-SFYZADRCSA-N

物化性质

• 沸点：
  233.1±33.0 °C(predicted)
• 密度：
  0.96±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,4R)-4-(Methylamino)cycloheptanol 在 氯化亚砜 作用下， 生成 莨菪烷
  参考文献：
  名称：

  Manipulation of substituents at nitrogen in tropanes, homotropanes, and dehydro- derivatives

  摘要：

  Trop-6-ene (8-methyl-8-azabicyclo[3.2.1]oct-6-ene) and substituted N-benzylnortrop-6-enes are synthesised. N-Debenzylation of tropanes fails using a wide variety of non-hydrogenolytic conditions despite effective application in model piperidine derivatives; debenzylation of homotropanes is more successful, giving norhomotropane and norhomotrop-7-ene. Bridged N-benzyl compounds react more slowly than N-methyl analogues with chloroformates; the resulting quaternary intermediates are more prone than the N-methyl analogues to suffer competitive reversion to the starting amine, especially in the tropanes, consistent with slower S(N)2 attack at the benzylic carbon during decomposition; the use of an N-p-methoxybenzyl group does allow partial debenzylation to nortrop-6-ene, suggesting greater SNI character in the decomposition step in this case. 'Equatorial' attack is preferred in methylation of N-benzyl-nortrop-6-ene and -homotrop-7-ene with CH3I; subsequent reductive debenzylation of the quaternary salt achieves overall replacement of N-benzyl by N-methyl in both cases. VT NMR studies show the presence of a single 'equatorial' invertomer (Cl syn- to the 2C-bridge) in N-chloro-norhomotropanes and -7-enes and, by analogy, in the N-alkyl compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00643-7
• 作为产物：
  描述：

  8-oxa-9-azabicyclo<3.2.2>non-6-ene hydrochloride 在 20percent Pd(OH)2/C lithium aluminium tetrahydride 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 81.5h， 生成 (1S,4R)-4-(Methylamino)cycloheptanol
  参考文献：
  名称：

  Hall, Adrian; Bailey, Patrick D.; Rees, David C., Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 329 - 343

  摘要：

  DOI：

文献信息

• Asymmetric cycloadditions of dienes to chloronitroso compounds derived from carbohydrate ketones: syntheses of (−)-physoperuvine and (+)-epibatidine
  作者：Adrian Hall、Patrick D. Bailey、Richard H. Wightman、David C. Rees

  DOI：10.1039/a806326e

  日期：——

  An α-chloronitroso compound derived from D-xylose undergoes cycloadditions with cyclic dienes to give bicyclic dihydrooxazines of high enantiomeric purity; such adducts were used in a synthesis of (–)-physoperuvine and a formal synthesis of (+)-epibatidine, whilst a pseudoenantiomeric chloronitroso compound is also available from L-sorbose.

  由D-木糖衍生的一种α-氯亚硝基化合物与环状二烯烃进行环加成反应，生成高对映纯度的双环二氢嗪嗪类化合物；这些加成产物曾用于合成(–)毒箭木碱和形式合成(+)-棘蛙毒素，同时也可从L-山梨糖获得一种伪对映体的氯亚硝基化合物。
• Synthesis of physoperuvine (8-methyl-8-azabicyclo[3.2.1]octan-1-ol), norphysoperuvine and dehydro-derivates
  作者：David E. Justice、John R. Malpass

  DOI：10.1039/p19940002559

  日期：——

  4-Aminocycloheptanones have been synthesised in high yield from cyclohepta-1,3-diene. These compounds exist mainly as the bicyclic tautomers (8-azabicyclo[3.2.1 ]octan-1-ol derivatives; the title compounds) as shown by 13C NMR spectroscopy at low temperatures. 4-Aminocyclohept-2enones are reactive but show a preference for the monocyclic tautomers; N-benzyloxycarbonyl derivatives of the saturated and

  已经从环庚-1，3-二烯高产率地合成了4-氨基环庚酮。这些化合物主要以双环互变异构体（8-氮杂双环[3.2.1]辛烷-1-醇衍生物；标题化合物）的形式存在，如低温下的13 C NMR光谱所示。4-Aminocyclohept-2enones具有反应性，但对单环互变异构体表现出偏爱；分离出饱和和不饱和体系的N-苄氧基羰基衍生物作为单环互变异构体。