(R)-(+)-methyl 3-oxocyclopentylacetate | 84621-34-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-(+)-methyl 3-oxocyclopentylacetate
• 英文别名: (R)-Methyl (3-oxocyclopentyl)acetate；(+)-3-oxocyclopentane-1-acetate；(R)-Methyl 2-(3-oxocyclopentyl)acetate；methyl 2-[(1R)-3-oxocyclopentyl]acetate
• CAS: 84621-34-1
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: CPXMFVOUUXTIOH-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-methyl 3-oxocyclopentylacetate 、 Hydroxyazanium;chloride 、 乙醇 、 吡啶 以95%的产率得到
  参考文献：
  名称：

  BREHM, RENATE;OHNHAUSER, DIETER;GERLACH, HANS, HELV. CHIM. ACTA, 70,(1987) N 8, 1981-1987

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-3-cyclopentenone 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 生成 (R)-(+)-methyl 3-oxocyclopentylacetate
  参考文献：
  名称：

  稳定、可储存和可重复使用的不对称催化剂：用于催化不对称迈克尔反应的新型 La 连接 BINOL 配合物

  摘要：

  DOI：

  10.1021/ja001036u

文献信息

• Asymmetric michael additions of ester enolates to enantiomerically pure vinylic sulfoxides
  作者：Gary H. Posner、Moshe Weitzberg、Terence G. Hamill、Edward Asirvatham、He Cun-heng、Jon Clardy

  DOI：10.1016/s0040-4020(01)90581-2

  日期：1986.1

  donors to enantiomerically pure Michael acceptor cycloalkenone sulfoxides 1a and 1b and unsaturated lactone sulfoxides 3a and 3b. The level of asymmetric induction in some cases is extraordinarily high (95% e.e. of final 1,5-dicarbonyl products). Adduct ester lactones 5 and 6 can be converted easily into some synthetically versatile, trifunctional, 3-substituted glutarate esters of high enantiomeric purity

  各种酯烯酸酯离子作为迈克尔供体加入对映体纯的迈克尔受体环烯酮亚砜1a和1b和不饱和内酯亚砜3a和3b。在某些情况下，不对称诱导的水平非常高（最终的1,5-二羰基产物的ee为95％）。加合物酯内酯5和6可以很容易地转化为一些具有高对映体纯度的合成上通用的三官能3取代的戊二酸酯。提出了对映体纯的戊烯内酯亚砜（S）-（+）- 3b的有效途径。
• Asymmetric Michael Addition Reaction of Phosphorus-Stabilized Allyl Anions with Cyclic Enones
  作者：Scott E. Denmark、Jung-Ho Kim

  DOI：10.1021/jo00128a028

  日期：1995.11

  The asymmetric Michael addition reaction of chirally modified P-allyl anions derived from enantiomerically enriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides has been investigated with cyclic enones. The racemic 1,3,2-oxazaphosphorinane 2-oxide 3 has been shown to be extremely diastereoselective in the Michael addition to 5-, 6-, and 7-ring enones. With the enantiomerically enriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides, high regio- and diastereoselectivities (88-90% diastereomeric excess) have been achieved in the Michael addition reaction of one of the diastereomers (cis series). The Michael reaction of the anions derived from the trans series were not diastereoselective (similar to 10% diastereomeric excess). The origin of the addition selectivity can be rationalized by (1) consideration of the structure and conformational preferences of the allyl anion (parallel conformation, s-trans, no lithium contact), (2) conformational analysis of the 1,3,2-oxazaphosphorinane 2-oxide ring (chair, equatorial allyl group) and (3) assumption of a 10-membered ring transition state structure with lithium coordination of the enone.
• Chiroptical studies of labile or difficult-to-resolve molecules generated by chiral laser photochemistry. 2. Products and steric course of the phototransformation of the racemate
  作者：Maurizio Zandomeneghi、Marino Cavazza、Crescenzo Festa、Francesco Pietra

  DOI：10.1021/ja00345a026

  日期：1983.4
• BREHM, RENATE;OHNHAUSER, DIETER;GERLACH, HANS, HELV. CHIM. ACTA, 70,(1987) N 8, 1981-1987
  作者：BREHM, RENATE、OHNHAUSER, DIETER、GERLACH, HANS

  DOI：——

  日期：——
• TAKASU, MAYUMI;WAKABAYASHI, HIROAKI;FURUTA, KYOJI;YAMAMOTO, HISASHI, TETRAHEDRON LETT., 29,(1988) N 52, C. 6943-6946
  作者：TAKASU, MAYUMI、WAKABAYASHI, HIROAKI、FURUTA, KYOJI、YAMAMOTO, HISASHI

  DOI：——

  日期：——