2-hydroxyoctyl pivalate | 123290-32-4

• 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: 2-hydroxyoctyl pivalate
• 英文别名: 2-Hydroxyoctyl 2,2-dimethylpropanoate
• CAS: 123290-32-4
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: OLISRLSAMYACTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  2-hydroxyoctyl pivalate 在 咪唑 、 重铬酸吡啶 、 4 A molecular sieve 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 6-[Tert-butyl(dimethyl)silyl]oxydodec-1-en-5-ol
  参考文献：
  名称：

  Annonaceous Acetogenins from the Seeds of Annona squamosa. Non-adjacent Bis-tetrahydrofuranic Acetogenins.

  摘要：

  从番荔枝（Annona squamosa）种子的石油醚提取物中分离得到四种非邻位的双四氢呋喃型乙酰萘醌类化合物，分别命名为鳞皮番荔枝亭B（2）、C（3）、D（4）和E（5）。这些乙酰萘醌类化合物的结构是通过光谱证据确定的。鳞皮番荔枝亭B和D的立体化学为C-15/C-16-苏式，C-19/C-20-苏式，C-23/C-24-赤式，而鳞皮番荔枝亭C和E的立体化学为C-15/C-16-苏式，C-19/C-20-苏式，C-23/C-24-苏式。通过与合成的单四氢吡喃模型化合物进行13C-NMR对比，已证实所有这些乙酰萘醌类化合物，包括鳞皮番荔枝亭A，都具有C-12/C-15反式，C-20/C-23反式的立体化学结构。同时，本文还提出了对鳞皮番荔枝亭A的改进型13C-NMR归属。

  DOI：

  10.1248/cpb.42.1175
• 作为产物：
  描述：

  特戊酸氯甲酯 在 三氟化硼乙醚 、 sodium iodide 、 lithium chloride 、 锌 作用下， 以 丙酮 为溶剂， 反应 14.58h， 生成 2-hydroxyoctyl pivalate
  参考文献：
  名称：

  Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen

  摘要：

  Alpha-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2. They insert efficiently zinc dust in THF-DMSO (X = Br, 8-10-degrees-C, 6-10 h) affording the corresponding zinc organometallics at the a position to oxygen FG-RCH(ZnBr)(OAc). After the addition of the THF-soluble copper salt CuCN.2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with various classes of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields. Similarly, zinc organometallics at the a position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic alpha-chloromethyl (or alpha-chloroethyl) imides. After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides. The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36-95% yield.

  DOI：

  10.1021/jo00055a010

文献信息

• Nucleophilic reactivity of zinc and copper carbenoids. Part II
  作者：Paul Knochel、Tso Sheng Chou、Huai Gu Chen、Ming Chang P. Yeh、Michael J. Rozema

  DOI：10.1021/jo00283a006

  日期：1989.10
• Knochel Paul, Chou Tso-Sheng, Jubert Carole, Rajagopal Duddu, J. Org. Chem., 58 (1993) N 3, S 588-599
  作者：Knochel Paul, Chou Tso-Sheng, Jubert Carole, Rajagopal Duddu

  DOI：——

  日期：——
• Annonaceous Acetogenins from the Seeds of Annona squamosa. Non-adjacent Bis-tetrahydrofuranic Acetogenins.
  作者：Yoshinori FUJIMOTO、Chikako MURASAKI、Hiroyasu SHIMADA、Seiichi NISHIOKA、Katsumi KAKINUMA、Sanjewon SINGH、Manorama SINGH、Yogesh Kumar GUPTA、Mahendra SAHAI

  DOI：10.1248/cpb.42.1175

  日期：——

  Four non-adjacent bis-tetrahydrofuranic acetogenins, named squamostatins-B (2), -C (3), -D (4) and -E (5), have been isolated from the petroleum ether extract of Annona squamosa seeds. The structures of these acetogenins have been established on the basis of spectral evidence. C-15/C-16-threo, C-19/C-20-threo, C-23/C-24-erythro stereochemistry was assigned for squamostatins-B and -D, whereas C-15/C-16-threo, C-19/C-20-threo, C-23/C-24-threo stereochemistry was assigened for squamostatins-C and -E. All of these acetogenins, including squamostatin-A, have been established to have C-12/C-15-trans, C-20/C-23-trans stereochemistry by 13C-NMR comparison with synthetic model mono-tetrahydrofuranic compounds. An improved <13>C-NMR assignment of squamostatin-A is presented.

  从番荔枝（Annona squamosa）种子的石油醚提取物中分离得到四种非邻位的双四氢呋喃型乙酰萘醌类化合物，分别命名为鳞皮番荔枝亭B（2）、C（3）、D（4）和E（5）。这些乙酰萘醌类化合物的结构是通过光谱证据确定的。鳞皮番荔枝亭B和D的立体化学为C-15/C-16-苏式，C-19/C-20-苏式，C-23/C-24-赤式，而鳞皮番荔枝亭C和E的立体化学为C-15/C-16-苏式，C-19/C-20-苏式，C-23/C-24-苏式。通过与合成的单四氢吡喃模型化合物进行13C-NMR对比，已证实所有这些乙酰萘醌类化合物，包括鳞皮番荔枝亭A，都具有C-12/C-15反式，C-20/C-23反式的立体化学结构。同时，本文还提出了对鳞皮番荔枝亭A的改进型13C-NMR归属。
• Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen
  作者：Paul Knochel、Tso Sheng Chou、Carole Jubert、Duddu Rajagopal

  DOI：10.1021/jo00055a010

  日期：1993.1

  Alpha-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2. They insert efficiently zinc dust in THF-DMSO (X = Br, 8-10-degrees-C, 6-10 h) affording the corresponding zinc organometallics at the a position to oxygen FG-RCH(ZnBr)(OAc). After the addition of the THF-soluble copper salt CuCN.2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with various classes of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields. Similarly, zinc organometallics at the a position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic alpha-chloromethyl (or alpha-chloroethyl) imides. After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides. The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36-95% yield.