(3R)-3-methylazacyclodecane | 435277-63-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (3R)-3-methylazacyclodecane
• 英文别名: (3R)-methylazacyclodecane；(3R)-3-methylazecane
• CAS: 435277-63-7
• 化学式: C₁₀H₂₁N
• 分子量: 155.283
• InChiKey: XAVGEVIBENPYFK-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3R)-3-methylazacyclodecane 在 镍 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、3.5 MPa 条件下， 生成 (+)-(3R)-1-(3-aminopropyl)-3-methylazacyclodecane
  参考文献：
  名称：

  Asymmetric synthesis of isohaliclorensin, a key intermediate of bisquinolinylpyrrole alkaloid halitulin

  摘要：

  A new enantioselective total synthesis of N-(3'-aminopropyl)-3-methylazacyclodecane, a partial structure of halitulin, has been achieved in eight steps with 14% overall yield. The key steps are the photochemical ring-expansion reaction of spirooxaziridine to lactam for constructing the azacyclodecane moiety and 1,4-stereoinductive methylation of the resulting lactam. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00007-1
• 作为产物：
  描述：

  (1'R)-1-(2'-methoxy-1'-phenylethyl)-3-methyl-azacyclodecane 在 palladium dihydroxide lithium aluminium tetrahydride 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、6.0 MPa 条件下， 以0.306 g的产率得到(3R)-3-methylazacyclodecane
  参考文献：
  名称：

  Asymmetric synthesis of isohaliclorensin, a key intermediate of bisquinolinylpyrrole alkaloid halitulin

  摘要：

  A new enantioselective total synthesis of N-(3'-aminopropyl)-3-methylazacyclodecane, a partial structure of halitulin, has been achieved in eight steps with 14% overall yield. The key steps are the photochemical ring-expansion reaction of spirooxaziridine to lactam for constructing the azacyclodecane moiety and 1,4-stereoinductive methylation of the resulting lactam. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00007-1

文献信息

• Callyazepin and (3<i>R</i>)-Methylazacyclodecane, Nitrogenous Macrocycles from a <i>Callyspongia</i> sp. Sponge
  作者：Chang-Kwon Kim、Jung-Kyun Woo、Yeon-Ju Lee、Hyi-Seung Lee、Chung J. Sim、Dong-Chan Oh、Ki-Bong Oh、Jongheon Shin

  DOI：10.1021/acs.jnatprod.5b01078

  日期：2016.4.22

  analyses revealed that the structure of 1 is a bicyclic azepane ammonium salt of a novel structural class derived from mixed biogenetic origins. The configuration of the whole molecule and the conformation of the formamide group were assigned by proton–proton coupling constants, a NOESY analysis, and the application of the phenylglycine methyl ester method. The structure of 2 was identified using combined

  从热带的Callyspongia sp。中分离出含氮大环的Callyazepin（1）和（3 R）-甲基氮杂环癸烷（2）。海绵。组合光谱分析表明，1的结构是源自混合生物遗传起源的新型结构类别的双环氮杂pan铵盐。通过质子-质子偶合常数，NOESY分析和苯基甘氨酸甲酯法的应用来指定整个分子的构型和甲酰胺基的构象。2的结构结合光谱分析和ECD测量进行鉴定。这些化合物对K562和A549细胞系表现出中等的细胞毒活性。
• Asymmetric synthesis of isohaliclorensin, a key intermediate of bisquinolinylpyrrole alkaloid halitulin
  作者：Yoshinosuke Usuki、Hiroyuki Hirakawa、Kimihiko Goto、Hideo Iio

  DOI：10.1016/s0957-4166(02)00007-1

  日期：2001.12

  A new enantioselective total synthesis of N-(3'-aminopropyl)-3-methylazacyclodecane, a partial structure of halitulin, has been achieved in eight steps with 14% overall yield. The key steps are the photochemical ring-expansion reaction of spirooxaziridine to lactam for constructing the azacyclodecane moiety and 1,4-stereoinductive methylation of the resulting lactam. (C) 2002 Elsevier Science Ltd. All rights reserved.