(6R,7R)-6-(benzyloxy)-7-hydroxynonan-2-one | 80502-06-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (6R,7R)-6-(benzyloxy)-7-hydroxynonan-2-one
• 英文别名: (6R,7R)-6-benzyloxy-7-hydroxynonan-2-one；(3R,4R)-4-O-(benzyloxy)-8-oxo-3-nonanol；(3R,4R)-4-(benzyloxy)-8-oxo-3-nonanol；(3R,4R)-4-benzyloxy-8-oxo-3-nonanol；(6R,7R)-7-hydroxy-6-phenylmethoxynonan-2-one
• CAS: 80502-06-3
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: SSHOMFFBFLTPQO-HZPDHXFCSA-N

物化性质

• 沸点：
  410.7±40.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6R,7R)-6-(benzyloxy)-7-hydroxynonan-2-one 在 钯 氢气 作用下， 以98%的产率得到(1R,7R)exo-brevicomin
  参考文献：
  名称：

  通过蒎二醇硼酸酯进行 99% 手性选择性合成：昆虫信息素、二醇和氨基醇

  摘要：

  合成这些特别是甲基-4 庚醇-3、短苯胺、eldanolide、癸二醇-5,6、甲基-6 十一烷二醇-5,7 和氨基-6 癸醇-5

  DOI：

  10.1021/ja00264a039
• 作为产物：
  描述：

  (2R,3R,5S)-3-(benzyloxy)-5-methoxy-2-vinyltetrahydrofuran 在 镍 水 、 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.5h， 生成 (6R,7R)-6-(benzyloxy)-7-hydroxynonan-2-one
  参考文献：
  名称：

  Synthetic routes to 6,8-dioxabicyclo[3.2.1]octyl pheromones from D-glucose derivatives. 2. Synthesis of (+)-exo-brevicomin

  摘要：

  DOI：

  10.1021/jo00345a006

文献信息

• Synthesis of (+)-endo- and (+)-exo-brevicomin viaEnzyme-Mediated Hydrolysis of an Enol Ester
  作者：Kazutsugu Matsumoto、Natsuko Suzuki、Hiromiehi Ohta

  DOI：10.1016/s0040-4039(00)97268-x

  日期：1990.1

  Optically pure (+)-endo- and (+)-exo-brevicomin have been synthesized in short steps starting from α-hydroxy ketone derivative, (R)-4-benzyloxy-8-nonen-3-one (3), which was prepared via enzymatic hydrolysis of racemic enol ester 4..

  光学纯的（+）-内-和（+）-外-brevicomin已从α-羟基酮衍生物（R）-4-苄氧基-8-壬烯-3-一（3）出发在短时间内合成。通过外消旋烯醇酯4的酶促水解制备。
• Stereoselective total syntheses of (+)-exo- and (−)-exo-brevicomins, (+)-endo- and (−)-endo-brevicomins, (+)- and (−)-cardiobutanolides, (+)-goniofufurone
  作者：Pinki Pal、Arun K. Shaw

  DOI：10.1016/j.tet.2011.04.014

  日期：2011.6

  (−)-cardiobutanolide (14b), and (+)-goniofufurone (19a) were achieved in good yields from enantiomerically pure highly functionalized furanoid glycal building blocks (1a–d) involving similar synthetic strategies, thus making these furanoid glycals highly useful building blocks in diversity-oriented synthesis (DOS).

  聚集信息素（+）- exo -brevicomin（9a），（-）- exo -brevicomin（9b），（+）-内-brevicomin（9c），（-）- endo -brevicomin（9d）和苯乙烯内酯（+）-心脏丁醇内酯（14a），（-）-心脏丁醇内酯（14b）和（+）-goniofufurone（19a）是从对映体纯的高度官能化的呋喃类化合物糖基砌块（1a - d中获得的））涉及类似的合成策略，因此使这些呋喃类化合物糖类在面向多样性的合成（DOS）中成为非常有用的构建基块。
• Lewis acid catalysis of the homologation of boronic esters with
  申请人：Washington State University Research Foundation, Inc.

  公开号：US04525309A1

  公开（公告）日：1985-06-25

  Boronate complexes are rearranged in the presence of a Lewis acid catalyst to boronic esters, particularly .alpha.-haloboronic esters.

  硼酸配合物在路易斯酸催化剂的存在下重排成硼酸酯，尤其是α-卤代硼酸酯。
• Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: an enantioselective synthesis of (+)-exo-brevicomin
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2005.10.035

  日期：2005.12

  Enantioselective synthesis of alpha-hydroxy aldehydes with an alkene tether was accomplished front L-(+)-tartaric acid, employing stereoselective reduction of a 1,4-diketone with L-selectride as the key step. Synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromone (+)-exo-brevicomin. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of α-benzyloxy-ω-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (−)-isolaurepan
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2007.05.014

  日期：2007.7

  The enantioselective synthesis of alpha-benzyloxy aldehydes containing a terminal alkene was carried out from chiral Pool L-(+)tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromones (+)-exo-brevicomin, (+)-iso-exo-brevicomin and a formal synthesis of 2,7cis-disubstituted oxepane (-)-isolaurepan. (c) 2007 Elsevier Ltd. All rights reserved.