methyl 2-methyl-3-hydroxyhexanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 2-methyl-3-hydroxyhexanoate
• 英文别名: (+/-)-(2S*,3R*)-methyl 3-hydroxy-2-methylhexanoate；rac-(2R,3S)-methyl 3-hydroxy-2-methylhexanoate；methyl (2S,3R)-3-hydroxy-2-methylhexanoate
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: ZOXSNMQWSRADLU-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2-methyl-3-hydroxyhexanoyl)-2-benzoxazolinone 、 甲醇 在 4-二甲氨基吡啶 作用下， 以 甲醇 为溶剂， 以74%的产率得到methyl 2-methyl-3-hydroxyhexanoate
  参考文献：
  名称：

  N-Acyl-2-benzoxazolinones in titanium-mediated aldol reactions

  摘要：

  N-Acyl-2-benzoxazolinones readily form trichlorotitanium enolates that react rapidly with aldehydes to provide crystalline syn-aldol adducts in high yield. The resulting products are simply converted to amides, esters, and thioesters. A simple, economical synthesis of 3-hydroxy-2-methylpentanoate N-propionylcysteamine thioesters based on these findings is presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.029

文献信息

• Regioselective Carbonylation of <i>trans</i>-Disubstituted Epoxides to β-Lactones: A Viable Entry into <i>syn</i>-Aldol-Type Products
  作者：Michael Mulzer、Bryan T. Whiting、Geoffrey W. Coates

  DOI：10.1021/ja405151n

  日期：2013.7.31

  reported for the regioselective carbonylation of trans-disubstituted epoxides to cis-β-lactones. The two catalysts display high and opposing selectivities, which generally are difficult to achieve for this class of epoxides. The resulting β-lactones are well-defined precursors for a wide variety of aldol-type compounds. Altogether, carbonylation of disubstituted epoxides is established as a viable and

  据报道，两种新催化剂可用于将反式双取代环氧化物区域选择性羰基化成顺式-β-内酯。这两种催化剂显示出高且相反的选择性，这对于此类环氧化物通常难以实现。由此产生的 β-内酯是各种羟醛型化合物的明确前体。总之，双取代环氧化物的羰基化被确立为合成和抗羟醛产品的可行且经济的入口。
• Bornane sultam-directed asymmetric synthesis of crystalline, enantiomerically pure syn aldols
  作者：Wolfgang Oppolzer、Julian Blagg、Ines Rodriguez、Eric Walther

  DOI：10.1021/ja00163a045

  日期：1990.3

  La configuration absolue est controlee par le choix du centre ion (M=B, Li ou Sn(IV)) de l'enolate des N-acylsultames

  La configuration absolue est controlee par le choix du center ion (M=B, Li ou Sn(IV)) de l'enolate des N-acylsultames
• Asymmetric aldol reactions: a novel model for switching between chelation- and non-chelation-controlled aldol reactions
  作者：Tu Hsin Yan、Chang Wei Tan、Hui Chun Lee、Hua Chi Lo、Tzung Yu Huang

  DOI：10.1021/ja00060a010

  日期：1993.4

  A new camphor-based N-propionyloxazolidinethione provides remarkable levels of asymmetric induction for both chelation-and non-chelation-controlled aldol processes. While the aldol condensation of the derived di-n-butylboryl enolate with various aldehydes affords the 'Evans'' syn aldol with excellent diastereoselectivity, the chlorotitanium enolate gives the ''non-Evans' syn aldol expected from chelation control. Most noteworthy is the observation that the sense of facial selectivity from the chlorotitanium enolate of propionyloxazolidinethione is opposite to that obtained from propionyloxazolidinone. This important finding illustrates the importance of increased chelating potential of the enolate ligand, ring thiocarbonyl, in maximizing the aldol pi-facial discrimination. Final nondestructive chiral auxiliary removal via hydroperoxide-assisted hydrolysis and subsequent esterification provides enantiomerically pure methoxy-carbonyl aldols.
• Diastereoselectivity in heterogeneous catalytic hydrogenation of Baylis–Hillman adducts. Total synthesis of (±)-sitophilate
  作者：Cristiano R Mateus、Melissa P Feltrin、Ana M Costa、Fernando Coelho、Wanda P Almeida

  DOI：10.1016/s0040-4020(01)00647-0

  日期：2001.8

  We describe herein a highly diastereoselective total synthesis of racemic sitophilate, based on the results obtained in a diastereoselective heterogeneous catalytic hydrogenation reaction of a set of Baylis-Hillman adducts originating from aliphatic aldehydes. (C) 2001 Published by Elsevier Science Ltd.
• OPPOLZER, WOLFGANG;BLAGG, JULIAN;RODRIGUEZ, INES;WALTHER, ERIC, J. AMER. CHEM. SOC., 112,(1990) N, C. 2767-2772
  作者：OPPOLZER, WOLFGANG、BLAGG, JULIAN、RODRIGUEZ, INES、WALTHER, ERIC

  DOI：——

  日期：——