1-((1R,2R)-2-Methyl-1-oxo-1λ⁴-[1,3]dithian-2-yl)-ethanone | 131309-71-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 1-((1R,2R)-2-Methyl-1-oxo-1λ⁴-[1,3]dithian-2-yl)-ethanone
• 英文别名: 1-[(1R,2R)-2-methyl-1-oxo-1,3-dithian-2-yl]ethanone
• CAS: 131309-71-2
• 化学式: C₇H₁₂O₂S₂
• 分子量: 192.303
• InChiKey: YKFFXILIAMVKLN-RDDDGLTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-((1R,2R)-2-Methyl-1-oxo-1λ⁴-[1,3]dithian-2-yl)-ethanone 在 sodium tetrahydroborate 作用下， 以91%的产率得到1-((1R,2R)-2-Methyl-1-oxo-1λ⁴-[1,3]dithian-2-yl)-ethanol
  参考文献：
  名称：

  Chiral dithiolane sulphoxides: An efficient stereoselective synthesis of (R) and (S)-3-benzoyloxy-2-butanone

  摘要：

  The effect of the addition of water on the asymmetric oxidation of an acyl dithiane and an acyl dithiolane has been studied. The use of enantiomerically pure dithiolane sulphoxides is demonstrated in a highly selective synthesis of (R)-3-benzoyloxy-2-butanone which depends upon a diastereoselective ketone reduction.

  DOI：

  10.1016/0040-4039(95)01280-u
• 作为产物：
  描述：

  1-(2-methyl-[1,3]dithian-2-yl)-ethanone 、 L-(+)-酒石酸二乙酯 生成 1-((1R,2R)-2-Methyl-1-oxo-1λ⁴-[1,3]dithian-2-yl)-ethanone
  参考文献：
  名称：

  BULMAN, PHILIP C.;NAMWINDWA, ERNEST S.;KLAIR, SUKHBINDER S.;WESTWOOD, DON+, SYNLETT.,(1990) N, C. 457-459

  摘要：

  DOI：

文献信息

• Enantioselective preparation of 2-substituted- 1,3-dithiane 1-oxides using modified sharpless sulphoxidation procedures
  作者：Philip C. Bulman Page、Robin D. Wilkes、Emest S. Namwindwa、Michael J. Witty

  DOI：10.1016/0040-4020(95)01029-7

  日期：1996.2

  carried out using modified Sharpless conditions to furnish the corresponding sulphoxides in optically enriched form. Deacylation of 2-acyl-1,3-dithiane 1-oxide derivatives allows the preparation of 2-alkyl-1,3-dithiane 1-oxides and the parent 1,3-dithiane 1-oxide itself in high enantiomeric excesses.

  已经使用改良的Sharpless条件进行了范围广泛的2-取代的1,3-二硫杂环丁烷的对映选择性磺氧化，以提供光学富集形式的相应亚砜。2-酰基-1,3-二硫杂环丁烷1-氧化物衍生物的脱酰作用可以制备2-烷基-1,3-二硫杂环丁烷1-氧化物和母体1,3-二硫杂环丁烷1-氧化物本身以高对映体过量的方式制备。
• Synthesis and Some Reactions of 2-Acyl-2-alkyl-1,3-dithiolane 1,1-Dioxides
  作者：M. Teresa Barros、António S. Henriques、Alcino J. Leitão、Christopher D. Maycock

  DOI：10.1002/1522-2675(200211)85:11<4079::aid-hlca4079>3.0.co;2-s

  日期：2002.11

  The selective formation of optically active 2-acyl-2-alkyl-1,3-dithiolane 1,1-dioxides from the corresponding 2-acyl-2-alkyl-1,3-dithiolane 1-oxides, by reaction with OsO4 and NMO in acetone, is reported. These compounds underwent stereoselective reactions at the carbonyl group of the acyl group with organometallic reagents. These reactions were completely regioselective, and no attack at either of

  通过与 OsO4 和 NMO 反应，由相应的 2-酰基-2-烷基-1,3-二硫杂环戊烷 1-氧化物选择性形成光学活性 2-酰基-2-烷基-1,3-二硫杂环戊烷 1,1-二氧化物据报道，在丙酮中。这些化合物在酰基的羰基上与有机金属试剂发生立体选择性反应。这些反应是完全区域选择性的，并且没有观察到对任何一个 S 原子的攻击，这与与相应亚砜的类似反应不同。金属原子的性质对产物醇的构型有直接影响。
• Enhanced diastereo and enantioselectivity in the formation of acyldithiolane sulphoxides by the asymmetric oxidation of their enolsilyl ethers
  作者：M.Teresa Barros、Alcino J. Leitão、Christopher D. Maycock

  DOI：10.1016/s0040-4039(97)01101-5

  日期：1997.7

  The sulphoxidation of the enol ethers of some acyldithiolanes using the Sharpless epoxidation reagents followed by fluorolysis results in better overall stereoselectivity than direct oxidation of the acyldithiolane thus providing a highly stereoselective route to acyldithiolane sulphoxides. Fluorolysis under acid conditions of non terminal enol ethers results in complete racemisation of the product. (C) 1997 Published by Elsevier Science Ltd.
• BULMAN, PHILIP C.;NAMWINDWA, ERNEST S.;KLAIR, SUKHBINDER S.;WESTWOOD, DON+, SYNLETT.,(1990) N, C. 457-459
  作者：BULMAN, PHILIP C.、NAMWINDWA, ERNEST S.、KLAIR, SUKHBINDER S.、WESTWOOD, DON+

  DOI：——

  日期：——
• Chiral dithiolane sulphoxides: An efficient stereoselective synthesis of (R) and (S)-3-benzoyloxy-2-butanone
  作者：M.Teresa Barros、Alcino J. Leitão、Christopher D. Maycock

  DOI：10.1016/0040-4039(95)01280-u

  日期：1995.9

  The effect of the addition of water on the asymmetric oxidation of an acyl dithiane and an acyl dithiolane has been studied. The use of enantiomerically pure dithiolane sulphoxides is demonstrated in a highly selective synthesis of (R)-3-benzoyloxy-2-butanone which depends upon a diastereoselective ketone reduction.