1-Azabicyclo<3.3.0>octan-4-ylmethyl benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Azabicyclo<3.3.0>octan-4-ylmethyl benzoate
• 英文别名: [(1S,8S)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl benzoate
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: AGMYGUKZAHBZSD-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Azabicyclo<3.3.0>octan-4-ylmethyl benzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以80%的产率得到(+/-) isoretronecanol
  参考文献：
  名称：

  Stereoselectivity in the photoinduced electron transfer (PET) promoted intramolecular cyclisations of 1-alkenyl-2-silyl-piperidines and -pyrrolidines: rapid construction of 1-azabicyclo[m.n.0]alkanes and stereoselective synthesis of (±)-isoretronecanol and (±)-epilupinine

  摘要：

  PET promoted cyclisations of 1-alkenyl-2-silyl-pyrrolidines and -piperidines 9a-d to 1-aza-bicyclo[m.n.0]alkanes have been found to be stereoselective. The five-membered ring formation gives predominantly cis products while six-membered rings are trans. Application of such cyclisations to the synthesis of (+/-)-isoretronecanol 22a, (+/-)-epilupinine 29 and related alkaloids has been demonstrated.

  DOI：

  10.1039/p19960000219
• 作为产物：
  描述：

  hexahydro-pyrrolizine-1-carboxylic acid ethyl ester 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 1-Azabicyclo<3.3.0>octan-4-ylmethyl benzoate
  参考文献：
  名称：

  Pandey, Ganesh; Lakshmaiah; Gadre, Smita R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 2, p. 91 - 98

  摘要：

  DOI：

文献信息

• Stereodivergent Synthesis of 1-Hydroxymethylpyrrolizidine Alkaloids
  作者：Abhijeet M. Sarkale、Chandrakumar Appayee

  DOI：10.1021/acs.orglett.0c01375

  日期：2020.6.5

  stereodivergent strategy for the asymmetric synthesis of all stereoisomers of 1-hydroxymethylpyrrolizidine alkaloids is developed using an asymmetric self-Mannich reaction as a key step. An anti-selective self-Mannich reaction of methyl 4-oxobutanoate with the PMP-amine catalyzed by a chiral secondary amine is successfully optimized for the asymmetric synthesis of (+)-isoretronecanol and (−)-isoretronecanol

  使用不对称的自我曼尼希反应作为关键步骤，开发了第一种立体异构策略，用于1-羟基甲基吡咯烷啶生物碱的所有立体异构体的不对称合成。成功地优化了4-氧代丁酸甲酯与手性仲胺催化的PMP-胺的抗选择性自曼尼希反应，以实现（+）-异戊烯醇和（-）-异丁烯醇的不对称合成。脯氨酸催化的顺选择性自曼尼希反应用于非对映异构体（+）-laburnine及其对映体（-）-trachelanthamidine的不对称合成。
• Ag(I)F as one electron oxidant for promoting sequential double desilylation : An ideal approach to non-stabilized azomethine ylides for the rapid construction of 1-azabicyclo (m:3:0) alkanes
  作者：Ganesh Pandey、G. Lakshmaiah

  DOI：10.1016/s0040-4039(00)74110-4

  日期：1993.7

  A novel methodology for effecting sequential double desilylation by Ag(I)F for the generation of non-stabilized azomethine ylide and its application for the synthesis of 1-azabicyclo(m.3.0) alkane systems are described.
• Structure of Monocrotaline. VIII. The Proof of Primary and Secondary Hydroxyl Groups in Retronecine¹
  作者：Roger Adams、K. E. Hamlin

  DOI：10.1021/ja01263a021

  日期：1942.11
• Men'schnikow; Kusowkow, Zhurnal Obshchei Khimii, 1949, vol. 19, p. 1702,1707;engl.Ausg.S.a137,a142
  作者：Men'schnikow、Kusowkow

  DOI：——

  日期：——
• Stereoselectivity in the photoinduced electron transfer (PET) promoted intramolecular cyclisations of 1-alkenyl-2-silyl-piperidines and -pyrrolidines: rapid construction of 1-azabicyclo[m.n.0]alkanes and stereoselective synthesis of (±)-isoretronecanol and (±)-epilupinine
  作者：Ganesh Pandey、Gottimukkula Devi Reddy、Debasish Chakrabarti

  DOI：10.1039/p19960000219

  日期：——

  PET promoted cyclisations of 1-alkenyl-2-silyl-pyrrolidines and -piperidines 9a-d to 1-aza-bicyclo[m.n.0]alkanes have been found to be stereoselective. The five-membered ring formation gives predominantly cis products while six-membered rings are trans. Application of such cyclisations to the synthesis of (+/-)-isoretronecanol 22a, (+/-)-epilupinine 29 and related alkaloids has been demonstrated.