yashabushidiol B (1,7-diphenylheptane-(3R)-(5R)-diol) | 103729-39-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: yashabushidiol B (1,7-diphenylheptane-(3R)-(5R)-diol)
• 英文别名: (3S,5S)-1,7-diphenyl-3,5-heptanediol；(3S,5S)-1,7-diphenylheptane-3,5-diol；(3S,5S)-1,7-diphenylhept-3,5-diol；(-)-yashabushidiol B；yashabushidiol B；yashabushidol
• CAS: 103729-39-1
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: QSUSPILNZCEGPK-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  yashabushidiol B (1,7-diphenylheptane-(3R)-(5R)-diol) 在 lithium aluminium tetrahydride 、 对甲苯磺酰氯 作用下， 生成 (R)-1,7-diphenyl-3-heptanol
  参考文献：
  名称：

  溶剂对 1,7-二芳基-5-羟基-3-庚酮及相关化合物旋光性的影响

  摘要：

  (S)-1,7-二苯基-5-羟基-3-庚酮、(S)-1,7-双(3,4-二甲氧基苯基)-5-羟基-3-庚酮的ORD和CD曲线，以及相关模型化合物是在选定的不同极性溶剂中获得的。导致 1,7-二芳基-5-羟基-3-庚酮在氯仿中右旋的原因是在 C-3 羰基和 C-5 羟基之间形成了分子内氢键，无论是否存在苯基组。另一方面，证明使化合物在甲醇中左旋需要同时破坏分子内氢键，然后溶剂化到羰基和/或羟基，以及苯基的存在。约。30% 的溶剂对旋光度的影响是基于随着溶剂的变化，与羰基的 n→π* 转变相关的旋转强度的变化。剩余的 70% 是基于与电子跃迁相关的旋转强度的变化......

  DOI：

  10.1246/bcsj.59.1181
• 作为产物：
  描述：

  2,4-戊二酮,1,5-二氯 在 Ru2Cl4{2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}2*N(C2H5)3 氢氧化钾 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， -78.0~102.0 ℃ 、8.62 MPa 条件下， 反应 4.67h， 生成 yashabushidiol B (1,7-diphenylheptane-(3R)-(5R)-diol)
  参考文献：
  名称：

  Optically pure 1,3-diols from (2R,4R)- and (2S,4S)-1,2:4,5-diepoxypentane

  摘要：

  Optically pure (> 97% ee) (2R,4R)-1,2:4,5-diepoxypentane (1) and its enantiomer can be prepared in three steps from 2,4-pentanedione without the need for chromatographic purification. Diepoxide 1 is an efficient precursor to a wide variety of optically pure syn and anti 1,3-diols. Reaction with excess nucleophile gives symmetric[GRAPHICS]anti 1,3-diols in good yield. Reaction with a slight excess of alkyllithium under Ganem's conditions gives the monoepoxides 5 in good yield. Addition of a second nucleophile to monoepoxide 5 gives asymmetric anti 1,3-diols. Mitsunobu inversion of monoepoxide 5 followed by addition of a second nucleophile gives syn 1,3-diols. Optically pure syn and anti 1,3-diols are available from diepoxide 1 in one to three steps and good overall yield.

  DOI：

  10.1021/jo00017a032

文献信息

• Double Catalytic Kinetic Resolution (DoCKR) of Acyclic <i>anti</i> -1,3-Diols: The Additive Horeau Amplification
  作者：Jérémy Merad、Prashant Borkar、Frédéric Caijo、Jean-Marc Pons、Jean-Luc Parrain、Olivier Chuzel、Cyril Bressy

  DOI：10.1002/anie.201709844

  日期：2017.12.11

  two successive enantioselective organocatalytic acylation reactions, and leads to diesters and recovered diols with high enantiopurities. It was first developed with C2‐symmetrical diols and then further extended to non‐C2‐symmetrical anti diols to prepare useful chiral building blocks. The protocol is highly practical as it only requires 1 mol % of a commercially available organocatalyst and leads

  本文所述的协同双催化动力学拆分（DoCKR）概念已成功应用于外消旋无环抗-1,3-二醇（天然产物中的常见基序）。该方法利用了涉及两个连续的对映选择性有机催化酰化反应的加性Horeau扩增的优势，并产生了具有高对映纯度的二酯和回收的二醇。它首先用C 2对称二醇开发，然后进一步扩展到非C 2对称抗氧化剂。二醇来制备有用的手性结构单元。该方案是高度实用的，因为它仅需要1 mol％的市售有机催化剂，并导致易于分离的产物。该程序用于报告的最短的全合成（+）-隐脂内酯，这是一种具有抗发芽活性的天然产物。
• Co-catalyzed two-stereocentered hydrolytic kinetic resolution: application to the synthesis of yashabushidiols A and B and the lactone unit of compactin and mevinolin
  作者：Sunita K. Gadakh、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2014.12.006

  日期：2015.2

  A short and efficient enantioselective synthesis of yashabushidiols A and B and the β-hydroxy-δ-lactone moiety of compactin and mevinolin with high enantiomeric purity (98% ee) is described starting from commercially available materials. The strategy mainly comprises of iodine-induced intramolecular electrophilic addition of a carbonate occurring in a highly diastereoselective fashion and the Co-catalyzed

  yashabushidiols A和B的一个短和高效对映选择性合成和康帕丁和洛伐他汀的具有高对映体纯度（98％ee）的β型羟基δ内酯基团被描述从市售材料开始。的策略主要包括碘诱导的分子内电子加成以高度非对映时尚和官能化的环氧化物作为手性诱导步骤的钴催化的两stereocentered水解动力学拆分发生的碳酸盐。
• Asymmetric Transfer Hydrogenation of Functionalized Acetylenic Ketones
  作者：Zhijia Fang、Martin Wills

  DOI：10.1021/jo401284c

  日期：2013.9.6

  A systematic study of the asymmetric transfer hydrogenations of functionalized acetylenic ketones and diketones has been completed, together with a total synthesis of (S,S)-(-)-yashabushidiol B. In several cases, excellent enantioselectivities and yields were achieved.
• Synthesis of yashabushidiol and its analogues and their cytotoxic activity against cancer cell lines
  作者：M. Narasimhulu、T. Srikanth Reddy、K. Chinni Mahesh、A. Sai Krishna、J. Venkateswara Rao、Y. Venkateswarlu

  DOI：10.1016/j.bmcl.2009.03.061

  日期：2009.6

  A total synthesis of yashabushidiol (1a), a linear diarylheptanoid having 1,3-diol system and its analogues has been achieved by alkynylation of 3-hydroxy-5-phenyl pentanal with substituted phenyl acetylenes. All the compounds have shown significant anti-proliferative activity on human leukemia (THP-1, U-937) and melanoma (A-375) cell lines. Compounds 2a and 2b were found to be most potent with an IC50 of 12.82 mu g/mL and 12.62 mu g/mL, respectively, on THP-1 leukemia cell line. (C) 2009 Elsevier Ltd. All rights reserved.
• The Solvent Effects on the Optical Rotatory Properties of 1,7-Diaryl-5-hydroxy-3-heptanones and Related Compounds
  作者：Shinji Ohta

  DOI：10.1246/bcsj.59.1181

  日期：1986.4

  the intramolecular hydrogen bond followed by solvation to the carbonyl and/or hydroxyl groups, as well as the presence of the phenyl groups. The ca. 30% of the solvent effect on the optical rotation was based on the change in the rotational strength associated with the n→π∗ transition of the carbonyl group as changing a solvent. The residual 70% was based on the change in the rotational strength associated

  (S)-1,7-二苯基-5-羟基-3-庚酮、(S)-1,7-双(3,4-二甲氧基苯基)-5-羟基-3-庚酮的ORD和CD曲线，以及相关模型化合物是在选定的不同极性溶剂中获得的。导致 1,7-二芳基-5-羟基-3-庚酮在氯仿中右旋的原因是在 C-3 羰基和 C-5 羟基之间形成了分子内氢键，无论是否存在苯基组。另一方面，证明使化合物在甲醇中左旋需要同时破坏分子内氢键，然后溶剂化到羰基和/或羟基，以及苯基的存在。约。30% 的溶剂对旋光度的影响是基于随着溶剂的变化，与羰基的 n→π* 转变相关的旋转强度的变化。剩余的 70% 是基于与电子跃迁相关的旋转强度的变化......