Diisopropyl γ-hydroxypimelate | 122950-94-1

• 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: Diisopropyl γ-hydroxypimelate
• 英文别名: diisopropyl 4-hydroxyheptanedioate；Dipropan-2-yl 4-hydroxyheptanedioate
• CAS: 122950-94-1
• 化学式: C₁₃H₂₄O₅
• 分子量: 260.331
• InChiKey: XTLMPIIYAHFNRX-UHFFFAOYSA-N

物化性质

• 沸点：
  346.6±37.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Diisopropyl γ-hydroxypimelate 在 咪唑 、 二异丁基氢化铝 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 1.17h， 生成 (E,E)-diethyl 6-(tert-butyldimethylsilyloxy)undeca-2,9-dienedioate
  参考文献：
  名称：

  Two-Directional Desymmetrization by Double 1,4-Addition of Silicon and Boron Nucleophiles

  摘要：

  The two-directional desymmetrization of prochiral precursors with alpha,beta-unsaturated branches by catalyst-controlled 1,4-addition of silicon and likewise boron nucleophiles allows for a general enantioselective access to syn,anti-triols with 1,n + 1,2n + 1 (n = 2 and 3) substitution patterns. The utility is demonstrated in the synthesis of the C17-C25 fragment of dermostatin A.

  DOI：

  10.1021/ol300832f
• 作为产物：
  描述：

  4-酮庚二酸 在 sodium tetrahydroborate 、 硫酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.0h， 生成 Diisopropyl γ-hydroxypimelate
  参考文献：
  名称：

  Lipase-catalyzed preparation of optically active .gamma.-butyrolactones in organic solvents

  摘要：

  DOI：

  10.1021/jo00298a031

文献信息

• Asymmetric synthesis of 5- and 6-membered lactones from cyclic substrates bearing a C2-chiral auxiliary
  作者：Yukio Yamamoto、Akio Sakamoto、Takaaki Nishioka、Junichi Oda、Yoshimasa Fukazawa

  DOI：10.1021/jo00003a038

  日期：1991.2

  Optically active lactones were synthesized by a novel asymmetric synthesis in which enantiotopic groups remote from a prochiral center were effectively discriminated. The cyclic diamide alcohols bearing a C2-chiral auxiliary, (+)-[1,1'-binaphthyl]-2,2'-diamine (4), were designed and prepared such that the hydroxyl group should attack preferentially at one of the two carbonyl groups. By the catalytic action of trifluoroacetic acid, the substrates 6a,b and 19 were smoothly converted to the lactones 7a (71% de), 7b (97% de), and 20 (> 99% de), the configurations of which were determined to be R, S, and R, respectively. A naturally occurring pheromone, (R)-(+)-5-hexadecanolide (13), was synthesized optically pure from 7b. Transition-state models for the present asymmetric lactonization were constructed according to the stereoelectronic theory proposed by Deslongchamps. The stability of the models was assessed by MM2 calculation, and the direction of asymmetric induction thus calculated coincided with the experimental results.
• GUTMAN, ARIE L.;ZUOBI, KHEIR;BRAVDO, TAMAR, J. ORG. CHEM., 55,(1990) N1, C. 3546-3552
  作者：GUTMAN, ARIE L.、ZUOBI, KHEIR、BRAVDO, TAMAR

  DOI：——

  日期：——