(3R)-6-(benzyloxy)hex-1-en-3-ol

• 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: (3R)-6-(benzyloxy)hex-1-en-3-ol
• 英文别名: (R)-6-(benzyloxy)-hex-1-en-3-ol；(3R)-6-phenylmethoxyhex-1-en-3-ol
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: HMPNYJBASMRXRZ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-6-(benzyloxy)hex-1-en-3-ol 在 咪唑 、 4-二甲氨基吡啶 、 萘 、 2,2,6,6-四甲基哌啶氧化物 、 lithium 、 氟化氢吡啶 、 iodobenzene diacetate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 12.0h， 生成 (1R)-1-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]octyl (4S)-4-hydroxyhex-5-enoate
  参考文献：
  名称：

  立体选择性全合成叶内酯

  摘要：

  描述了使用MacMillanα-羟基化，Steglic酯化和闭环复分解为关键步骤的二甲苯甲酸酯的立体选择性全合成。使用有机催化MacMillanα-羟基化来构建二氧内酯的两个手性中心使该方法具有吸引力。

  DOI：

  10.1016/j.tetlet.2013.08.038
• 作为产物：
  描述：

  (3R)-6-(benzyloxy)hex-1-yn-3-ol 在 喹啉 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以86%的产率得到(3R)-6-(benzyloxy)hex-1-en-3-ol
  参考文献：
  名称：

  Total synthesis of the phytotoxic stagonolides A and B

  摘要：

  The chemo-enzymatic and covergent synthesis of stagonolide B and the synthesis of stagonolide A, a phytotoxic 10-membered lactone have been achieved starting from D-ribose with overall yields of 25% and 8.7%, respectively. The synthesis contained simple steps in developing three centers' key intermediates, namely the enzymatic (Novozyme-435) resolution of a propargylic alcohol followed by macrolactonization and RCM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.010

文献信息

• Stereoselective Total Synthesis of Bistramide A
  作者：J. S. Yadav、Lakshindra Chetia

  DOI：10.1021/ol702095n

  日期：2007.10.1

  A highly stereoselective and convergent total synthesis of bistramide A is described. The salient feature of this synthesis is the construction of the spiroketal subunit by hydrolysis of dialkylated tosylmethyl isocyanide derivative derived via alkylation of TosMIC with suitably substituted halohydrin derivatives.

  描述了双立体酰胺A的高度立体选择性和收敛的全合成。该合成的显着特征是通过将TosMIC与合适取代的卤代醇衍生物进行烷基化而衍生的二烷基化的甲苯磺酰基甲基异氰化物衍生物的水解来构建螺环亚基。
• The Stereoselective Total Synthesis of (+)-Stagonolide B
  作者：Pabbaraja Srihari、Boyapelly Kumaraswamy、Ragam Somaiah、Jhillu Yadav

  DOI：10.1055/s-0029-1218638

  日期：2010.3

  The stereoselective total synthesis of the nonenolide, (+)-stagonolide B is described. The key steps involve epoxide homologation, hydrolytic kinetic resolution and ring-closing metathesis. macrolide - ring-closing metathesis - antifungal - phytotoxic - kinetic resolution

  描述了壬烯内酯（+）-甾烷醇化物B的立体选择性全合成。关键步骤涉及环氧化物的同源性，水解动力学拆分和闭环复分解。 大环内酯类-闭环复分解-抗真菌-植物毒性-动力学拆分
• Stereoselective Total Synthesis of Mangiferaelactone using<scp>D</scp>-Mannose as a Chiral Pool
  作者：Basi V. Subba Reddy、Pathuri Sivaramakrishna Reddy、Kummari Vijaya Babu、Bhemavarapu Phaneendra Reddy、Jhillu Singh Yadav

  DOI：10.1002/hlca.201500103

  日期：2015.10

  A convergent total synthesis of mangiferaelactone has been accomplished in a highly stereoselective manner from readily available D‐mannose. The following methods like organocatalytic enantioselective epoxidation, ring‐closing metathesis, and Steglich esterification have been employed as key steps, which make this approach more attractive.

  已从容易获得的D-甘露糖中以高度立体选择性的方式完成了芒果内酯的聚合全合成。以下方法（例如有机催化对映体选择性环氧化，闭环复分解和Steglich酯化）已被用作关键步骤，这使该方法更具吸引力。
• Stereoselective total synthesis of xyolide
  作者：B.V. Subba Reddy、P. Sivaramakrishna Reddy、B. Phaneendra Reddy、J.S. Yadav、Ahamad Al Khazim Al Ghamdi

  DOI：10.1016/j.tetlet.2013.08.038

  日期：2013.10

  A stereoselective total synthesis of xyolide is described employing MacMillan α-hydroxylation, Steglich esterification, and ring closing metathesis as key steps. The use of organocatalytic MacMillan α-hydroxylation to construct two of the chiral centers of the xyolide makes this approach attractive.

  描述了使用MacMillanα-羟基化，Steglic酯化和闭环复分解为关键步骤的二甲苯甲酸酯的立体选择性全合成。使用有机催化MacMillanα-羟基化来构建二氧内酯的两个手性中心使该方法具有吸引力。
• Total synthesis of the phytotoxic stagonolides A and B
  作者：Peddikotla Prabhakar、Singanaboina Rajaram、Dorigondla Kumar Reddy、Vanam Shekar、Yenamandra Venkateswarlu

  DOI：10.1016/j.tetasy.2010.01.010

  日期：2010.2

  The chemo-enzymatic and covergent synthesis of stagonolide B and the synthesis of stagonolide A, a phytotoxic 10-membered lactone have been achieved starting from D-ribose with overall yields of 25% and 8.7%, respectively. The synthesis contained simple steps in developing three centers' key intermediates, namely the enzymatic (Novozyme-435) resolution of a propargylic alcohol followed by macrolactonization and RCM. (C) 2010 Elsevier Ltd. All rights reserved.