(5S,1'S)-5-(1'-(dibenzylamino)ethyl)dihydrofuran-2(3H)-one | 133148-53-5

• 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: (5S,1'S)-5-(1'-(dibenzylamino)ethyl)dihydrofuran-2(3H)-one
• 英文别名: (5S)-5 [(1S)-1-(N,N-dibenzylamino)-ethyl]dihydrofuran-2(3H)-one；(5S)-5-[(1S)-1-(dibenzylamino)ethyl]oxolan-2-one
• CAS: 133148-53-5
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: LWZXGBJQLXCLJJ-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (5S,1'S)-5-(1'-(dibenzylamino)ethyl)dihydrofuran-2(3H)-one 在 钯 氢气 作用下， 以 乙醇 为溶剂， 生成 [(S)-1-((S)-5-Oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  非对映选择性合成关键内酯中间体，用于制备羟乙烯二肽等排体

  摘要：

  从α-N，N-二苄基氨基酮制备羟基乙烯二肽等排体的有效且高度立体选择性的途径已经开发出来。

  DOI：

  10.1016/s0040-4039(00)75834-5
• 作为产物：
  描述：

  (S)-5-Dibenzylamino-4-oxo-hexanoic acid tert-butyl ester 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (5S,1'S)-5-(1'-(dibenzylamino)ethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  非对映选择性合成关键内酯中间体，用于制备羟乙烯二肽等排体

  摘要：

  从α-N，N-二苄基氨基酮制备羟基乙烯二肽等排体的有效且高度立体选择性的途径已经开发出来。

  DOI：

  10.1016/s0040-4039(00)75834-5

文献信息

• Stereocontrolled convergent synthesis of hydroxyethylene dipeptide isosteres by the reaction of α-amino aldehyde with alkoxytitanium homoenolates
  作者：Shinzo Kano、Tsutomu Yokomatsu、Shiroshi Shibuya

  DOI：10.1016/0040-4039(91)80863-2

  日期：1991.1

  The reaction of (S)-α-dibenzylamino aldehydes with dichloroisopropoxytitanium ester homoenolates gave the corresponding γ-aminoalkyl γ-lactones with high erythro selectivity. The same reaction by the use of amide homoenolates also afforded the corresponding 2-amino alcohols with high erythro-selectivity.

  （S）-α-二苄基氨基醛与二氯异丙氧基钛酸酯均烯酸酯的反应得到相应的具有高赤型选择性的γ-氨基烷基γ-内酯。通过使用酰胺均烯酸酯的相同反应也提供了具有高赤型选择性的相应的2-氨基醇。
• Diastereoselective synthesis of hydroxyethylene dipeptide isosteres
  申请人：Emory University

  公开号：US05587514A1

  公开（公告）日：1996-12-24

  A process for the synthesis of hydroxyethylene dipeptide isosteres from .alpha.-N,N-di(protected)-amino(alkyl or substituted alkyl)methyl ketones that can be efficiently carried out on an industrial scale. The process proceeds with excellent diastereoselectivity and chemical efficiency, and can be used to prepare a wide variety of hydroxyethylene dipeptide isosteres for a variety of uses, including as HIV-1 protease inhibitors and renin inhibitors.

  一种从.alpha.-N,N-二（保护）-氨基（烷基或取代烷基）甲基酮合成羟基乙烯二肽类同构体的工艺，可在工业规模下高效地进行。该工艺具有优异的对映选择性和化学效率，并可用于制备各种羟基乙烯二肽类同构体，包括作为HIV-1蛋白酶抑制剂和肾素抑制剂等多种用途。
• Diastereoselective synthesis hydroxyethylene dipeptide isosteres
  申请人：Emory University

  公开号：US05990341A1

  公开（公告）日：1999-11-23

  A process for the synthesis of hydroxyethylene dipeptide isosteres from .alpha.-N,N-di(protected)amino(alkyl or substituted alkyl) methyl ketones that can be efficiently carried out on an industrial scale. The process proceeds with excellent diastereoselectivity and chemical efficiency, and can be used to prepare a wide variety of hydroxyethylene dipeptide isosteres for a variety of uses, including as HIV-1 protease inhibitors and renin inhibitors.

  一种从α-N,N-二(保护基)氨基(烷基或取代烷基)甲基酮合成羟基乙烯二肽同分异构体的方法，可在工业规模上高效进行。该方法具有优异的对映选择性和化学效率，并可用于制备各种羟基乙烯二肽同分异构体，包括作为HIV-1蛋白酶抑制剂和肾素抑制剂等多种用途。
• One-Step Highly Diastereoselective Synthesis of γ-Aminoalkyl-Substituted γ-Butyrolactones by an Asymmetric Samarium-Mediated Ketyl−Alkene Coupling Reaction
  作者：Shin-ichi Fukuzawa、Manabu Miura、Takahide Saitoh

  DOI：10.1021/jo020574h

  日期：2003.3.1

  The samarium(II) iodide mediated reaction of N,N-dibenzyl-protected (S)-alpha-amino aldehydes with (1S,2R)-N-methylephedrinyl acrylate gave the (4R,1'S)-gamma-(aminoalkyl)-gamma-butyrolactones in good yields with high diastereoselectivities (up to 80% de); (4R,1'S)-gamma-amino-(2-phenylethyl)-gamma-butyrolactone (6a), which should be a potent precursor for gamma-secretase inhibitors, was obtained with high de value.
• Hormuth, Stephan; Reissig, Hans-Ulrich; Dorsch, Dieter, Angewandte Chemie, 1993, vol. 105, # 10, p. 1513 - 1514
  作者：Hormuth, Stephan、Reissig, Hans-Ulrich、Dorsch, Dieter

  DOI：——

  日期：——