己酸,(3R,4S,5R)-3-羟基-8-羰基-1,7-二氧杂螺[4.4]壬-4-基酯 | 162341-13-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 己酸,(3R,4S,5R)-3-羟基-8-羰基-1,7-二氧杂螺[4.4]壬-4-基酯
• 英文名称: secosyrin 1
• 英文别名: [(3R,4S,5R)-3-hydroxy-8-oxo-1,7-dioxaspiro[4.4]nonan-4-yl] hexanoate
• CAS: 162341-13-1
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: BSPDBROUVLBHSZ-JIMOISOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	[(3R,4S,5R)-3-(methoxymethoxy)-8-oxo-1,7-dioxaspiro[4.4]nonan-4-yl] hexanoate	194476-28-3	C15H24O7	316.351
  ——	3,4-dihydroxy-1,7-dioxaspiro[4.4]nonan-8-one	197219-87-7	C7H10O5	174.153
  ——	(3R,4S,5R)-4-hydroxy-3-(methoxymethoxy)-1,7-dioxaspiro[4.4]nonan-8-one	194476-26-1	C9H14O6	218.207
  ——	3,4-bis(benzyloxy)-1,7-dioxaspiro[4.4]nonan-8-one	189328-24-3	C21H22O5	354.403
  ——	3,4-bis(benzyloxy)-6-hydroxy-1,7-dioxaspiro[4.4]nonan-8-one	1353888-95-5	C21H22O6	370.402
  ——	(3R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-1,7-dioxaspiro[4.4]nonan-8-one	194475-97-3	C13H24O5Si	288.416
  ——	(3R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-(methoxymethoxy)-1,7-dioxaspiro[4.4]nonan-8-one	194476-23-8	C15H28O6Si	332.469
  ——	methyl 4,5-bis(benzyloxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylate	1353888-63-7	C22H24O5	368.43

反应信息

• 作为反应物：
  描述：

  己酸,(3R,4S,5R)-3-羟基-8-羰基-1,7-二氧杂螺[4.4]壬-4-基酯 在 lithium hexamethyldisilazane 作用下， 生成 4-(1,2-dihydroxy-5-oxodecyl)furan-2(5H)-one
  参考文献：
  名称：

  First Total Synthesis of (+)-Secosyrin 1

  摘要：

  The first total synthesis of (+)-secosyrin 1, isolated from P. syringae. pv. tomato, was accomplished in a stereoselective manner from diisopropyl D-tartrate. This synthesis unambiguously established the stereochemistry of (+)-secosyrin 1. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00380-8
• 作为产物：
  描述：

  3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2H-furan-5-one 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 四丁基氟化铵 、 溶剂黄146 、 苯硫酚 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 45.08h， 生成 己酸,(3R,4S,5R)-3-羟基-8-羰基-1,7-二氧杂螺[4.4]壬-4-基酯
  参考文献：
  名称：

  Total Syntheses of Sphydrofuran, Secosyrins, and Syributins^,1

  摘要：

  Two groups of natural products, sphydrofuran (1) and its furan derivative (2) and secosyrins 1 and 2 (3a, 3b) and syributins 1 and 2 (4a, 4b), were synthesized from one precursor (6), which was realized starting from 3-tri-n-butylstannylfuran or 3-bromofuran.

  DOI：

  10.1021/jo970476+

文献信息

• Efficient synthesis of syringolides, secosyrins, and syributins through a common approach
  作者：Anastasia-Aikaterini C. Varvogli、Ioannis N. Karagiannis、Alexandros E. Koumbis

  DOI：10.1016/j.tet.2008.11.079

  日期：2009.1

  A new common synthetic approach toward the elicitors syringolides and their related natural products, secosyrins and syributins, is described here. This uses d-arabinose as starting material and efficiently delivers the targeted compounds through a sequential tandem HWE olefination–lactonization process and an IHMA reaction.

  本文介绍了诱导子丁香油苷及其相关天然产物，二十二醛和丁香苷的一种新的通用合成方法。它以d-阿拉伯糖为起始原料，并通过顺序的串联HWE烯化-内酯化过程和IHMA反应有效地递送目标化合物。
• A Short and Efficient Preparation of Enantiopure Secosyrins 1 and 2
  作者：Alexandros Koumbis、Anastasia-Aikaterini Varvogli

  DOI：10.1055/s-2006-951540

  日期：——

  An alternative, short and efficient approach for the preparation of enantiopure secosyrins 1 and 2 is reported here. This uses a d-arabinose derivative as starting material and applies a HWE-IHMA strategy for the construction of the spiro-framework of target molecules.

  本文报告了制备对映体纯刹那菊苷 1 和 2 的另一种简捷高效的方法。该方法使用 d-阿拉伯糖衍生物作为起始原料，并采用 HWE-IHMA 策略构建目标分子的螺框架。
• Stereoselective synthesis of (+)-secosyrin 1
  作者：D. Gautam、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2009.01.106

  日期：2009.4

  A Chiron approach for the synthesis of (+)-secosyrin 1 from D-mannitol has been described. The key steps are a stereoselective Wittig reaction and an intramolecular Michael addition on the disubstituted butenolide, leading to a highly stereoselective formation of the tertiary chiral centre of (+)-secosyrin 1. (C) 2009 Elsevier Ltd. All rights reserved.
• Wong, Henry N. C., European Journal of Organic Chemistry, 1999, # 8, p. 1757 - 1765
  作者：Wong, Henry N. C.

  DOI：——

  日期：——
• First Total Synthesis of (+)-Secosyrin 1
  作者：Chisato Mukai、Sameh M Moharram、Miyoji Hanaoka

  DOI：10.1016/s0040-4039(97)00380-8

  日期：1997.4

  The first total synthesis of (+)-secosyrin 1, isolated from P. syringae. pv. tomato, was accomplished in a stereoselective manner from diisopropyl D-tartrate. This synthesis unambiguously established the stereochemistry of (+)-secosyrin 1. (C) 1997 Elsevier Science Ltd.