(S)-(-)-methyl 3-oxocyclopentylacetate | 2630-38-8

• 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: (S)-(-)-methyl 3-oxocyclopentylacetate
• 英文别名: (S)-Methyl (3-oxocyclopentyl)acetate；methyl 3-oxocyclopentaneacetate；(-)-Methyl-3-oxocyclopentanacetat；(S)-Methyl 2-(3-oxocyclopentyl)acetate；methyl 2-[(1S)-3-oxocyclopentyl]acetate
• CAS: 2630-38-8
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: CPXMFVOUUXTIOH-LURJTMIESA-N

物化性质

• 沸点：
  85-95 °C(Press: 0.1 Torr)
• 密度：
  1.093±0.06 g/cm3(Predicted)

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

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  (S)-(-)-methyl 3-oxocyclopentylacetate 、 (2R,3R)-(-)-2,3-丁二醇 以53%的产率得到
  参考文献：
  名称：

  POSNER G. H.; WEITZBERG M.; HAMILL T. G.; ASIRVATHAM E.; CUN-HENG HE; CLA+, TETRAHEDRON, 42,(1986) N 11, 2919-2929

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,2S,3R)-3-Hydroxy-2-(methoxycarbonyl)cyclopentanessigsaeure-methylester 在 chromium(VI) oxide 、 盐酸 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 (S)-(-)-methyl 3-oxocyclopentylacetate
  参考文献：
  名称：

  Absolute configuration of endo-cis-bicyclo[3.3.0]oct-7-en-2-ol and specific rotation of 3-oxocyclopentaneacetic acid

  摘要：

  DOI：

  10.1021/jo01317a034

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。
• Organocatalytic Enantioselective Michael Additions of Malonates to 2-Cyclopentenone
  作者：Nobuyuki Mase、Maho Fukasawa、Norihiko Kitagawa、Fumiya Shibagaki、Naoyasu Noshiro、Kunihiko Takabe

  DOI：10.1055/s-0030-1258533

  日期：2010.9

  The Michael reaction of a dialkyl malonate to a cyclic enone using a chiral diamine/acid combination catalyst gave the desired Michael adduct in high yield with excellent enantiomeric excess in a protic solvent such as methanol and ethanol. The methanol molecule participates in a proton relay system in which the dialkyl malonate is activated through hydrogen bonding to afford the Michael adduct with

  使用手性二胺/酸组合催化剂，丙二酸二烷基酯与环烯酮的迈克尔反应以高产率得到所需的迈克尔加合物，在质子溶剂（如甲醇和乙醇）中具有极好的对映体过量。甲醇分子参与质子中继系统，其中丙二酸二烷基酯通过氢键活化，提供具有优异对映选择性的迈克尔加合物。
• METHODS OF PREPARING ALPHA,BETA-UNSATURATED OR ALPHA-HALO KETONES AND ALDEHYDES
  申请人：International Flavors & Fragrances Inc.

  公开号：EP3184504A1

  公开（公告）日：2017-06-28

  Copper(II) bromide mediated oxidation of acylated enol and use of the reaction in the synthesis of α,β-unsaturated or α-bromo ketones or aldehydes are disclosed. The method provides an efficient and practical process for manufacturing dehydrohedione (DHH) and many other versatile α,β-unsaturated or α-bromo ketones or aldehydes in large scales to avoid using precious metal compounds.

  本发明公开了由溴化铜（II）介导的酰化烯醇氧化反应，以及利用该反应合成α,β-不饱和或α-溴酮或醛的方法。该方法为大规模生产脱氢双酮（DHH）和许多其他多功能α,β-不饱和或α-溴酮或醛提供了一种高效实用的工艺，从而避免了使用贵金属化合物。
• 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