(S)-2-(2-hydroxy-2-phenylethyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-one | 158732-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-(2-hydroxy-2-phenylethyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-one
• 英文别名: 2-[(2R)-2-hydroxy-2-phenylethyl]-1,5-dioxaspiro[5.5]undec-2-en-4-one
• CAS: 158732-43-5
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: GLDNTHIVJKXNNL-OAHLLOKOSA-N

物化性质

• 沸点：
  497.7±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-hydroxy-2-phenylethyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-one 在 咪唑 、 水 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 (R)-4-(tert-butyldimethylsiloxy)-4-phenyl-2-butanone
  参考文献：
  名称：

  Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines: Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst.

  摘要：

  通过手性酒石酸衍生的酰基硼烷介导的源自 6-甲基的硅烯醇醚的醇醛缩合，完成了在 6 位具有 2-羟基化烷基的 1, 3-二恶英-4-酮的新型对映选择性合成-1, 3-二恶英-4-酮与非手性醛的衍生物。

  DOI：

  10.1248/cpb.42.839
• 作为产物：
  描述：

  4-甲基-1,5-二氧杂螺[5.5]十一碳-3-烯-2-酮 在 正丁基锂 、 monoacylated tartaric acid-borane complex (CAB complex-6b) 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-2-(2-hydroxy-2-phenylethyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-one
  参考文献：
  名称：

  Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines: Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst.

  摘要：

  通过手性酒石酸衍生的酰基硼烷介导的源自 6-甲基的硅烯醇醚的醇醛缩合，完成了在 6 位具有 2-羟基化烷基的 1, 3-二恶英-4-酮的新型对映选择性合成-1, 3-二恶英-4-酮与非手性醛的衍生物。

  DOI：

  10.1248/cpb.42.839

文献信息

• Nonlinear effects and auto-induction in the asymmetric aldol condensation of synthetic equivalents of acetoacetic esters
  作者：Rosaria Villano、Margherita De Rosa、Concetta Salerno、Annunziata Soriente、Arrigo Scettri

  DOI：10.1016/s0957-4166(02)00539-6

  日期：2002.9

  (+)-NLEs, have been detected in the Ti(IV)/BINOL complex-mediated catalytic asymmetric aldol reaction of three different masked acetoacetate esters. The use of a different procedure for the catalyst preparation disclosed the occurrence of aldol condensation of Chan's diene through an auto-inductive process.

  在三种不同掩蔽的乙酰乙酸酯的Ti（IV）/ BINOL络合物介导的催化不对称羟醛反应中已检测到正非线性效应（+）-NLE。使用不同的方法制备催化剂表明通过自动感应方法发生了陈氏二烯的醛醇缩合反应。
• A convenient catalytic procedure for the highly enantioselective aldol condensation of O-silyldienolates
  作者：Margherita De Rosa、Maria Rosaria Acocella、Rosaria Villano、Annunziata Soriente、Arrigo Scettri

  DOI：10.1016/s0957-4166(03)00494-4

  日期：2003.9

  In the presence of catalytic amount of chiral Ti(OiPr)(4)/BINOL (0.08 equiv.) the asymmetric aldol condensation of 6-methyl-4H-[1,3]-dioxin-4-one-derived silyloxydienes takes place in high yields and enantiomeric excesses with aromatic. heteroaromatic, Unsaturated and aliphatic aldehydes. Notable amplification of enantiomeric excesses have been obtained by using enantioenriched catalytic systems. (C) 2003 Elsevier Ltd. All rights reserved.
• Enantioselective aldol condensation of O-silyl dienolates to aldehydes mediated by chiral BINOL–titanium complexes
  作者：Margherita De Rosa、Annunziata Soriente、Arrigo Scettri

  DOI：10.1016/s0957-4166(00)00259-7

  日期：2000.8

  Chiral BINOL-titanium complexes have been shown to catalyze enantioselective aldol reactions between dioxinone derivatives and a set of aldehydes. The aldol adducts are isolated in good yields and high enantioselectivities. A range of substitution patterns on the O-silyl dienolate is possible: alkyl and benzyl substituents are tolerated. A simple reaction protocol is described and provides an efficient alternative to the well-known methods for conducting enantioselective Mukaiyama aldol reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Sato, Masayuki; Sunami, Satoshi; Sugita, Yoshiaki, Heterocycles, 1995, vol. 41, # 7, p. 1435 - 1444
  作者：Sato, Masayuki、Sunami, Satoshi、Sugita, Yoshiaki、Kaneko, Chikara

  DOI：——

  日期：——
• Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines: Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst.
  作者：Masayuki SATO、Satoshi SUNAMI、Yoshiaki SUGITA、Chikara KANEKO

  DOI：10.1248/cpb.42.839

  日期：——

  A novel enantioselective synthesis of 1, 3-dioxin-4-ones having a 2-hydroxylated alkyl group at the 6-position has been accomplished by chiral tartaric acid-derived acylborane-mediated aldol condensation of the silyl enol ether derived from 6-methyl-derivatives of 1, 3-dioxin-4-one with achiral aldehydes.

  通过手性酒石酸衍生的酰基硼烷介导的源自 6-甲基的硅烯醇醚的醇醛缩合，完成了在 6 位具有 2-羟基化烷基的 1, 3-二恶英-4-酮的新型对映选择性合成-1, 3-二恶英-4-酮与非手性醛的衍生物。