trans-trans-Deca-2,8-diendisaeure-diethylester | 15898-70-1

• 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: trans-trans-Deca-2,8-diendisaeure-diethylester
• 英文别名: 2,8-Decadienedioic acid, diethyl ester；diethyl (2E,8E)-deca-2,8-dienedioate
• CAS: 15898-70-1
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: SRXSLKRTMGRQDT-WGDLNXRISA-N

物化性质

• 沸点：
  348.4±42.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-trans-Deca-2,8-diendisaeure-diethylester 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 癸二酸二甲酯
  参考文献：
  名称：

  mediated intramolecular reductive cyclization of activated dienes

  摘要：

  Facile intramolecular cyclisation of activated tethered dienes mediated by magnesium in methanol at room temperature is described.

  DOI：

  10.1016/0040-4039(95)00190-n
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 己二醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以87%的产率得到trans-trans-Deca-2,8-diendisaeure-diethylester
  参考文献：
  名称：

  α，β-不饱和醛的有机催化[4 + 2]和[3 + 3]环加成反应合成芳香醛

  摘要：

  描述了α，β-不饱和醛的有机催化的分子间和分子内[4 + 2]和[3 + 3]环加成以得到多取代的芳族醛。观察到对环加成反应的高选择性是由l-脯氨酸和吡咯烷-HOAc产生的催化剂作用，以及助催化剂的加成作用。

  DOI：

  10.1016/j.tet.2007.01.039

文献信息

• A facile reductive dimerization of conjugated acid derivatives with samarium diiodide
  作者：Junji Inanaga、Yuich Handa、Takanori Tabuchi、Kenji Otsubo、Masaru Yamaguchi、Takeshi Hanamoto

  DOI：10.1016/0040-4039(91)80220-z

  日期：1991.11

  Conjugated esters were instantaneously hydrodimerized at room temperature by use of the reduction system, Sml2-THF-HMPA, in the presence of proton sources. A perfect stereoselection was realized in the reaction of N,N-dibenzyl crotonamide.

  在质子源的存在下，通过使用还原系统Sml 2 -THF-HMPA，在室温下将共轭酯瞬时加氢二聚。在N，N-二苄基巴豆酰胺的反应中实现了理想的立体选择。
• Cyclisation of α,β,γ,ψ-unsaturated dioic acid esters via tandem conjugate additions by using lithium N-benzyltrimethylsilylamide (LSA) as a nitrogen nucleophile and its application to a total synthesis of (±)-dihydronepetalactone and (±)-isodihydronepetalactone
  作者：Tadao Uyehara、Naomi Shida、Yoshinori Yamamoto

  DOI：10.1039/c39890000113

  日期：——

  A stereoselective total synthesis of (±)-dihydronepetalactone and (±)-isodihydronepetalactone has been accomplished by utilising a novel cyclisation procedure; a reaction of octadiene-2,6-dioic acid esters with lithium N-benzyltrimethylsilylamide (LSA) induces 5-exo-Trig ring-closure via tandem conjugate additions.

  （±）-二氢荆芥内酯和（±）-异二氢荆芥内酯的立体选择性全合成已经通过利用新颖的环化方法完成。辛二烯-2,6-二酸酯与N-苄基三甲基甲硅烷基氨基锂（LSA）的反应通过串联共轭物加成引发5-exo-Trig闭环。
• One-Pot O₂-Oxidation and the Horner–Wadsworth–Emmons Reaction of Primary Alcohols for the Synthesis of (<i>Z</i>)-α,β-Unsaturated Esters
  作者：Kaori Ando、Chika Takaba、Masahiro Kodama

  DOI：10.1021/acs.joc.2c00763

  日期：2022.8.5

  primary alcohols giving Z-α,β-unsaturated esters 3. TEMPO-(CuCl or CuBr2)-(2,2′-bipyridine) (1:1:1) catalyzed O2 oxidation of primary alcohols in the presence of Z-selective Horner–Wadsworth–Emmons reagent 1b and K3PO4 or NaH gave 3 with Z/E = 84:16 to 96:4 in high yields. A stepwise reaction was also developed. After TEMPO-CuBr2-(2,2′-bipyridine)-K3PO4 (1:1:1:1) catalyzed O2 oxidation of alcohols in MeCN

  我们开发了伯醇的一锅氧化/烯化程序，得到Z -α,β-不饱和酯3。TEMPO-(CuCl 或 CuBr 2 )-(2,2'-联吡啶) (1:1:1) 在Z选择性 Horner-Wadsworth-Emmons 试剂1b和 K 3 PO 4存在下催化伯醇的 O 2氧化或 NaH以Z / E = 84:16 至 96:4 的高产率得到3 。还开发了逐步反应。TEMPO-CuBr 2 -(2,2'-联吡啶)-K 3 PO 4 (1:1:1:1)催化O 2后在 MeCN 中氧化醇，所得混合物在 -78 °C 至 0 °C 下用1b和t -BuOK 的 THF 溶液处理，得到具有更高选择性的3 ( Z / E = 91:9 至 99:1)。
• New type of cyclization of .alpha.,.beta.,.chi.,.psi.-unsaturated dioic acid esters through tandem conjugate additions by using lithium N-benzyl-N-(trimethylsilyl)amide as a nitrogen nucleophile
  作者：Tadao Uyehara、Naomi Shida、Yoshinori Yamamoto

  DOI：10.1021/jo00037a034

  日期：1992.5

  Treatment of dimethyl (2E,6E)-2,6-octadienedioate with lithium N-benzyl-N-(trimethylsilyl)amide (LSA) gave 5-exo-trig ring closure products, methyl 3-(N-benzylamino)-2-(methoxycarbonyl)cyclopentane-1-acetates, through tandem conjugate additions. The related 6-exo-trig cyclization proceeded stereoselectively to give ethyl c-3-(N-benzylamino)-t-2-(ethoxycarbonyl)cyclohexane-1-acetate. In contrast with the 5- and 6-exo-trig cyclization, no 7-exo-trig cyclization occurred. The 5-exo-trig cyclization products were converted into 2-(methoxycarbonyl)-2-cyclopentene-1-carboxylic acid methyl ester in an excellent yield. 5-exo-trig cyclization of the unsymmetrical dienedioate consisting of crotonate and (E)-2-methyl-2-butenoate units proceeded regioselectively through conjugate addition of LSA to the crotonate part. Similar regioselectively was observed in the case of 5-exo-trig cyclization of the dienedioate possessing crotonate and (E)-3-methyl-2-pentenoate units. Total syntheses of the physiologically active cyclopentane monoterpenes (+/-)-dihydronepetalactone and (+/-)-isohydronepetalactone has been accomplished by this cyclization strategy. In addition, it has been demonstrated that LSA is a more efficient nitrogen nucleophile than LDA to cyclize omega-halo-alpha,beta-unsaturated esters.
• Ruthenium-catalyzed oxidative cyclization of 1,7-dienes. A novel diasteroselective synthesis of 2,7-disubstituted trans-oxepane diols
  作者：Vincenzo Piccialli、Nicola Borbone、Giorgia Oliviero

  DOI：10.1016/j.tetlet.2007.05.078

  日期：2007.7

  The ruthenium-catalyzed oxidation of some representative 1,7-dienes has been investigated. Tetrasubstituted 1,7-dienes are transformed into the corresponding trans-2,7-bis-hydroxyalkyl-oxepanes through an oxidative cyclization process. The process proceeds with an excellent stereo selectivity level. (C) 2007 Elsevier Ltd. All rights reserved.