(2S,6R)-2-tert-Butyl-6-methyl-[1,3]dioxan-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2S,6R)-2-tert-Butyl-6-methyl-[1,3]dioxan-4-one
• 英文别名: (2S,6R)-2-tert-butyl-6-methyl-1,3-dioxan-4-one
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: SFWUTHYTQUXJTB-SVRRBLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,6R)-2-tert-Butyl-6-methyl-[1,3]dioxan-4-one 在 acetylacetonatodicarbonylrhodium(l) 、 diclazuril 、 一氧化碳 、 2-叔丁基苯酚亚磷酸盐 、 氢气 、 重水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Unusual conformational effects on the regioselectivity of olefin insertion in the rhodium-catalyzed hydroformylation of 4-methylene-1,3-dioxanes

  摘要：

  A mechanistic model for the rhodium-catalyzed hydroformylation of 4-methylene-1,3-dioxanes is described. As part of a study aimed at an anti-diastereoselective hydroformylation, unusual conformational effects on the regioselectivity of the reaction were discovered. This discovery has led to the proposal that the product mixtures are governed by classical Curtin-Hammett kinetics. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01351-3
• 作为产物：
  描述：

  甲基锂 、 2-tert-Butyl-[1,3]dioxin-4-one 在 copper(l) iodide 作用下， 以89%的产率得到(2S,6R)-2-tert-Butyl-6-methyl-[1,3]dioxan-4-one
  参考文献：
  名称：

  Unusual conformational effects on the regioselectivity of olefin insertion in the rhodium-catalyzed hydroformylation of 4-methylene-1,3-dioxanes

  摘要：

  A mechanistic model for the rhodium-catalyzed hydroformylation of 4-methylene-1,3-dioxanes is described. As part of a study aimed at an anti-diastereoselective hydroformylation, unusual conformational effects on the regioselectivity of the reaction were discovered. This discovery has led to the proposal that the product mixtures are governed by classical Curtin-Hammett kinetics. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01351-3

文献信息

• Absolute Configurations of Melanoxadin, MR-93A, Melanoxazal, and MR-93B
  作者：Tian-Jun He、Shijun Zhu、Xiao-Wei Lu、Yikang Wu、Yan Li

  DOI：10.1002/ejoc.201403287

  日期：2015.1

  Fungal metabolites melanoxadin, MR-93A, melanoxazal, and MR-93B were synthesized with the key stereogenic centers derived from commercially available chiral building blocks. The optically active synthetic products with well-defined absolute configurations provided authentic samples for the stereoisomers of these oxazole-containing natural products and thus allowed for unambiguous assignments of their

  真菌代谢物 melanoxadin、MR-93A、melanoxazal 和 MR-93B 是用衍生自市售手性构件的关键立体中心合成的。具有明确定义的绝对构型的旋光合成产品为这些含恶唑的天然产物的立体异构体提供了可靠的样品，因此可以明确分配它们的相对和绝对构型。讨论了天然和纯合成样品之间旋光度的巨大差异。之前报告的 NMR 信号分配中的一些错误也得到了纠正。
• Seebach, Dieter; Imwinkelried, Rene; Stucky, Gerhard, Angewandte Chemie, 1986, vol. 98, # 2, p. 182 - 183
  作者：Seebach, Dieter、Imwinkelried, Rene、Stucky, Gerhard

  DOI：——

  日期：——
• Unusual conformational effects on the regioselectivity of olefin insertion in the rhodium-catalyzed hydroformylation of 4-methylene-1,3-dioxanes
  作者：Stella T. Sarraf、James L. Leighton

  DOI：10.1016/s0040-4039(98)01351-3

  日期：1998.9

  A mechanistic model for the rhodium-catalyzed hydroformylation of 4-methylene-1,3-dioxanes is described. As part of a study aimed at an anti-diastereoselective hydroformylation, unusual conformational effects on the regioselectivity of the reaction were discovered. This discovery has led to the proposal that the product mixtures are governed by classical Curtin-Hammett kinetics. (C) 1998 Elsevier Science Ltd. All rights reserved.