(S)-2-Ethyl-1,4-dioxa-spiro[4.5]decane-2-carbaldehyde | 155988-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-Ethyl-1,4-dioxa-spiro[4.5]decane-2-carbaldehyde
• 英文别名: (3S)-3-ethyl-1,4-dioxaspiro[4.5]decane-3-carbaldehyde
• CAS: 155988-02-6
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: JGQRLEMRZJIUAB-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-Ethyl-1,4-dioxa-spiro[4.5]decane-2-carbaldehyde 在 palladium dihydroxide 四丁基氟化铵 、 氢气 、 对甲苯磺酰氯 、 lithium hexamethyldisilazane 作用下， 以 三乙胺 为溶剂， 生成 5-[(R)-2-Ethyl-5-((R)-2-ethyl-1,4-dioxa-spiro[4.5]dec-2-yl)-pentylsulfanyl]-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  The first total synthesis and absolute stereochemistry of plakortone G from the Jamaican sponge Plakortis sp.

  摘要：

  Total synthesis of plakortone G (1), a secondary metabolite of the Jamaican sponge Plakortis sp., was successfully achieved. The absolute configuration of this molecule was determined by comparison of the synthetic diastereomers with reported data to possess the (4R,8R)-configuration 14. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.169
• 作为产物：
  描述：

  环己酮二甲缩酮 在 pyridine-SO3 complex 、 camphor-10-sulfonic acid 、 potassium carbonate 、 二甲基亚砜 作用下， 以 甲醇 、 三乙胺 为溶剂， 生成 (S)-2-Ethyl-1,4-dioxa-spiro[4.5]decane-2-carbaldehyde
  参考文献：
  名称：

  The first total synthesis and absolute stereochemistry of plakortone G from the Jamaican sponge Plakortis sp.

  摘要：

  Total synthesis of plakortone G (1), a secondary metabolite of the Jamaican sponge Plakortis sp., was successfully achieved. The absolute configuration of this molecule was determined by comparison of the synthetic diastereomers with reported data to possess the (4R,8R)-configuration 14. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.169

文献信息

• Anomalous enantioselectivity in the Sharpless catalytic asymmetric dihydroxylation reaction of 1,1-disubstituted allyl alcohol derivatives
  作者：Karl J. Hale、Soraya Manaviazar、S.Andrew Peak

  DOI：10.1016/0040-4039(94)85071-2

  日期：1994.1

  The Sharpless asymmetric dihydroxylation (AD) reaction has been examined on a number of 1,1-disubstituted allyl alcohol derivatives. In the majority of substrates studied, the product diols had ee's in the 11–91% range and had absolute stereochemistry opposite to that predicted using the Sharpless steric model.

  已对许多1,1-二取代的烯丙醇衍生物进行了Sharpless不对称二羟基化（AD）反应。在研究的大多数底物中，产物二醇的ee在11–91％范围内，并且绝对立体化学与使用Sharpless空间模型预测的相反。