(R)-4-benzyloxy-1-(pivaloyl)oxy-2-butanol | 500318-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-4-benzyloxy-1-(pivaloyl)oxy-2-butanol
• CAS: 500318-50-3
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: VMMGTLORQBELEB-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-4-benzyloxy-1-(pivaloyl)oxy-2-butanol 在 lithium aluminium tetrahydride 作用下， 生成 (S)-4-benzyloxy-2-butanol
  参考文献：
  名称：

  Acceleration of hetero-Michael reaction by symmetrical pentacyclic guanidines

  摘要：

  Symmetrical pentacyclic guanidines 1a-c and 2 which contain the core skeleton of 13,14,15-isocrmbescidine 800, have been synthesized. In the presence of catalytic amounts of these guanidines 1, the reaction rate of the conjugate addition of pyrrolidine (9) to gamma -crotonolactone (10) could be enhanced depending upon the size of the cavities and substituents on tetrahydropyran rings of 1 and 2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00907-3
• 作为产物：
  描述：

  三甲基乙酰氯 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (R)-4-benzyloxy-1-(pivaloyl)oxy-2-butanol
  参考文献：
  名称：

  Acceleration of hetero-Michael reaction by symmetrical pentacyclic guanidines

  摘要：

  Symmetrical pentacyclic guanidines 1a-c and 2 which contain the core skeleton of 13,14,15-isocrmbescidine 800, have been synthesized. In the presence of catalytic amounts of these guanidines 1, the reaction rate of the conjugate addition of pyrrolidine (9) to gamma -crotonolactone (10) could be enhanced depending upon the size of the cavities and substituents on tetrahydropyran rings of 1 and 2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00907-3

文献信息

• Studies directed toward the total synthesis of pinnatoxin A: synthesis of the 6,5,6-dispiroketal (BCD ring) system by double hemiketal formation/hetero-Michael addition strategy
  作者：Seiichi Nakamura、Jun Inagaki、Masashi Kudo、Tomohiro Sugimoto、Kohei Obara、Makoto Nakajima、Shunichi Hashimoto

  DOI：10.1016/s0040-4020(02)01379-0

  日期：2002.12

  An efficient, highly stereoselective synthesis of the C10–C26 portion of pinnatoxin A has been achieved, wherein the key step is a highly stereoselective construction of the 6,5,6-dispiroketal (BCD ring) system by an intramolecular hetero-Michael addition of a hemiketal alkoxide reversibly formed under the influence of lithium methoxide.

  品纳毒素A C10-C26部分的高效，高度立体选择性合成已经实现，其中关键步骤是通过分子内杂原子-迈克尔加成反应实现6,5,6-二螺酮（BCD环）系统的高度立体选择性构建。在甲醇锂的作用下可逆地形成的半烷醇盐。