5(Z)-decene-1,10-diol | 126412-06-4

• 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: 5(Z)-decene-1,10-diol
• 英文别名: 1,10-dihydroxy-5(Z)-decene；cis-dec-5-ene-1,10-diol；(Z)-dec-5-ene-1,10-diol
• CAS: 126412-06-4
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: CEUQFOBZFQQQRF-UPHRSURJSA-N

物化性质

• 沸点：
  299.3±33.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  5(Z)-decene-1,10-diol 在 吡啶 、 sodium hydroxide 、 四丁基碘化铵 、 sodium naphthalenide 作用下， 以 乙二醇二甲醚 、 水 、 苯 为溶剂， 反应 7.0h， 生成 氮杂环十一碳-6-烯,(6Z)-
  参考文献：
  名称：

  Manzamine C及其几何异构体的全合成

  摘要：

  Manzamine C（1）是由甲硅烷基氧乙烯（3）沿以下路线合成的：4→5→8→18→1。总产率为21％。通过14的Bischler-Napieralski反应，然后进行脱水，可得到Thrβ-咔啉链段（11）。通过类似的步骤，已经合成了反式异构体2和二氢马扎明C（21）。

  DOI：

  10.1016/s0040-4020(01)91003-8
• 作为产物：
  描述：

  1,5-环辛二烯 在 盐酸 、 sodium tetrahydroborate 、 potassium tert-butylate 、 水 、 双氧水 、 ortho-tungstic acid 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.5h， 生成 5(Z)-decene-1,10-diol
  参考文献：
  名称：

  Enantioselective Haloetherification by Asymmetric Opening of meso-Halonium Ions

  摘要：

  A new approach to enantioselective haloetherification reactions via desymmetrization of in situ-generated meso-halonium ions is described. The combination of N-haloamides as a halogen source and sodium salts of chiral phosphoric acids as catalysts can be used for the cyclization of symmetrical ene-diol substrates, yielding the haloetherification products under practical conditions in enantioenriched form.

  DOI：

  10.1021/ol1028805

文献信息

• Enantioselective Synthesis of 15-Deoxy-Δ^12,14-Prostaglandin J₂
  作者：Jiaming Li、Brian M. Stoltz、Robert H. Grubbs

  DOI：10.1021/acs.orglett.9b04198

  日期：2019.12.20

  An enantioselective synthesis of 15-deoxy-Δ12,14-prostaglandin J2 is reported. The synthesis begins with the preparation of enantiopure 3-oxodicyclopentadiene by a lipase-mediated kinetic resolution. A three-component coupling followed by a retro-Diels-Alder reaction provides the C8 stereochemistry of the prostaglandin skeleton with high enantioselectivity. Stereoretentive olefin metathesis followed

  报道了15-脱氧-Δ12，14-前列腺素J2的对映选择性合成。合成开始于通过脂肪酶介导的动力学拆分制备对映体纯的3-氧二环戊二烯。三组分偶联后进行逆Diels-Alder反应，可为前列腺素骨架提供高对映选择性的C8立体化学。立体定向烯烃复分解，然后进行Pinnick氧化，可以得到高对映体纯度的15-脱氧-Δ12,14-前列腺素J2。
• Concise Syntheses of Δ¹²-Prostaglandin J Natural Products via Stereoretentive Metathesis
  作者：Jiaming Li、Tonia S. Ahmed、Chen Xu、Brian M. Stoltz、Robert H. Grubbs

  DOI：10.1021/jacs.8b12816

  日期：2019.1.9

  Δ12-Prostaglandin J family is recently discovered and has potent anticancer activity. Concise syntheses of four Δ12-prostaglandin J natural products (7-8 steps in the longest linear sequences) are reported, enabled by convergent stereoretentive cross-metathesis. Exceptional control of alkene geometry was achieved through stereoretention.

  Δ12-前列腺素 J 家族最近被发现并具有有效的抗癌活性。报告了四种 Δ12-前列腺素 J 天然产物（最长线性序列中的 7-8 步）的简明合成，通过会聚立体保留交叉复分解实现。通过立体保留实现了对烯烃几何形状的特殊控制。
• A total synthesis of manzamine c
  作者：Yasuhiro Torisawa、Akihiro Hashimoto、Masako Nakagawa、Tohru Hino

  DOI：10.1016/s0040-4039(01)89018-3

  日期：——
• <i>Z</i>-Selective Ethenolysis with a Ruthenium Metathesis Catalyst: Experiment and Theory
  作者：Hiroshi Miyazaki、Myles B. Herbert、Peng Liu、Xiaofei Dong、Xiufang Xu、Benjamin K. Keitz、Thay Ung、Garik Mkrtumyan、K. N. Houk、Robert H. Grubbs

  DOI：10.1021/ja4010267

  日期：2013.4.17

  The Z-selective ethenolysis activity of chelated ruthenium metathesis catalysts was investigated with experiment and theory. A five-membered chelated catalyst that was successfully employed in Z-selective cross metathesis reactions has now been found to be highly active for Z-selective ethenolysis at low ethylene pressures, while tolerating a wide variety of functional groups. This phenomenon also affects its activity in cross metathesis reactions and prohibits crossover reactions of internal olefins via trisubstituted ruthenacyclobutane intermediates. In contrast, a related catalyst containing a six-membered chelated architecture is not active for ethenolysis and seems to react through different pathways more reminiscent of previous generations of ruthenium catalysts. Computational investigations of the effects of substitution on relevant transition states and ruthenacyclobutane intermediates revealed that the differences of activities are attributed to the steric repulsions of the anionic ligand with the chelating groups.
• Inhibition of Protein Kinase Cα by Dequalinium Analogues:  Dependence on Linker Length and Geometry
  作者：Donghui Qin、Regina Sullivan、William F. Berkowitz、Robert Bittman、Susan A. Rotenberg

  DOI：10.1021/jm990340z

  日期：2000.4.6

  Analogues of a bipartite compound, dequalinium (DECA) (quinolinium, 1,1'-(1,10-decanediyl)bis(4-amino-2-methyl diiodide)), were tested for inhibition of protein kinase C alpha (PKC alpha). In vitro assays of monomeric and dimeric analogues support a model in which DECA inhibits PKC alpha by an obligatory two-point contact, a unique mechanism among PKC inhibitors. The presence of unsaturation in the center of the C-10-alkyl linker produced geometric isomers with different inhibitory potencies: cis IC50 = 52 +/- 12 mu M and trans IC50 = 12 +/- 3 mu M, where the trans isomer was equipotent to that of the saturated C-10-DECA. DECA analogues with longer, saturated linkers (C-12, C-14, or C-16) exhibited enhanced inhibitory potencies which reached a plateau with the C-14-linker (IC50 = 2.6 +/- 0.2 mu M) Metastatic melanoma cells treated with 250 nM C-12-, C-14-, or C-16-DECA and irradiated with long-wave UV light (which causes irreversible inhibition of PKC alpha by DECA) confirmed the linker-dependent inhibition of intracellular PKC alpha activity.