(4S)-2-methylnon-1-en-4-ol | 153254-12-7

• 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: (4S)-2-methylnon-1-en-4-ol
• 英文别名: (S)-2-methyl-1-nonen-4-ol；(S)-2-methyl-1-nonene-4-ol
• CAS: 153254-12-7
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: BEJVHQKILDZJPX-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (4S)-2-methylnon-1-en-4-ol
  参考文献：
  名称：

  Catalytic asymmetric allylation using a chiral (acyloxy)borane complex as a versatile Lewis acid catalyst

  摘要：

  In the presence of 20 mol % of a chiral (acyloxy)borane (CAB) complex prepared from (2R,3R)-2-O-(2,6-diisopropoxybenzoyl)tartaric acid and borane-tetrahydrofuran, various allyltrimethylsilanes react with achiral aldehydes to afford the corresponding homoallylic alcohols in good yields with high diastereo- and enantioselectivities. Furthermore, the reactivity of allylation can be improved without reducing the enantioselelctivity by using 10-20 mol % of the CAB complex prepared from 3,5-bis(trifluoromethyl)phenylboronic acid and chiral tartaric acid derivative. The observed selectivities and re-face attack of nucleophiles on the carbonyl carbons of aldehydes imply that the extended transition-state model is applicable.

  DOI：

  10.1021/ja00077a054

文献信息

• A practical and efficient method for enantioselective allylation of aldehydes
  作者：E. J. Corey、Chan Mo Yu、Sung Soo Kim

  DOI：10.1021/ja00196a082

  日期：1989.7

  La reaction d'(allyl-2 diphenyl-4,5 ditosyl-1,3)diazaborolidines-1,3,2 chirales avec des aldehydes fournit des alcools homoallyliques de maniere enantioselective

  La 反应 d'(allyl-2 diphenyl-4,5 ditosyl-1,3)diazaborolidines-1,3,2 手性 avec des aldehydes Fournit des alcools homoallyliques de maniere enantioselective
• Asymmetric Catalysis of Nozaki−Hiyama Allylation and Methallylation with A New Tridentate Bis(oxazolinyl)carbazole Ligand
  作者：Masahiro Inoue、Takahiro Suzuki、Masahisa Nakada

  DOI：10.1021/ja021243p

  日期：2003.2.1

  the asymmetric catalysis of Nozaki-Hiyama allylation and methallylation. Various aldehydes were allylated or methallylated with good enantioselectivity (86-96%), and a key intermediate of calcitriol lactone synthesis was also obtained with excellent diastereoselectivity (97% de, 91%). The enantioselective reaction catalyzed by this Cr-ligand complex is applicable to a broad range of aldehydes and has

  这项工作描述了对 Nozaki-Hiyama 烯丙基化和甲基烯丙基化的不对称催化有效的新三齿配体的开发。各种醛以良好的对映选择性（86-96%）烯丙基化或甲基烯丙基化，并以优异的非对映选择性（97% de, 91%）获得骨化三醇内酯合成的关键中间体。由这种 Cr-配体配合物催化的对映选择性反应适用于广泛的醛类，在天然产物合成方面具有巨大潜力。这种配体的另一个显着特征是 Cr-配体复合物的稳定性，它在对映选择性反应后回收并循环两次，而不会降低对映选择性和产率。
• Bidirectional Asymmetric Allylboration. A Convenient Asymmetric Synthesis of <i>C</i>₂-Symmetric 3-Methylenepentane-1,5-diols and Rapid Access to <i>C</i>₂-Symmetric Spiroketals
  作者：Anthony G. M. Barrett、D. Christopher Braddock、Pieter D. de Koning、Andrew J. P. White、David J. Williams

  DOI：10.1021/jo991205x

  日期：2000.1.1

  single-crystal X-ray study of bis-Mosher ester 6g. Desymmetrization and further functionalization of diol 1a were achieved by treatment of the bis-BOC carbonate 13 with IBr in toluene at -80 degrees C to give cyclic iodocarbonate 14 as a single diastereomer. This methodology is also applicable in natural product synthesis; enantiomerically pure spiroketals 1,7-dioxaspiro[5.5]undecanes 18 and 25, the latter

  在布朗的无盐条件下，使用1，3-双（二异樟脑硼基硼基）-2-亚甲基丙烷（R，R）-3和（S，S）-3进行醛的双烯丙基硼化可提供C（2）-对称的3-亚甲基戊烷- 1,5-二醇1对映体过量。通过双-双酯6g的单晶X射线研究证实了产品的绝对立体化学。通过在-80℃下用IBr在甲苯中处理双-BOC碳酸酯13，得到二醇1a的不对称化和进一步官能化，得到环状碘代碳酸酯14，为单一非对映异构体。这种方法也适用于天然产物的合成。对映体纯的螺环酮1,7-二氧杂螺[5.5]十一烷18和25，后者代表海绵体20的AB环系统的简便合成方法，
• Weigand, Stefan; Brueckner, Reinhard, Chemistry - A European Journal, 1996, vol. 2, # 9, p. 1077 - 1084
  作者：Weigand, Stefan、Brueckner, Reinhard

  DOI：——

  日期：——
• Catalytic asymmetric allylation using a chiral (acyloxy)borane complex as a versatile Lewis acid catalyst
  作者：Kazuaki Ishihara、Makoto Mouri、Qingzhi Gao、Tohru Maruyama、Kyoji Furuta、Hisashi Yamamoto

  DOI：10.1021/ja00077a054

  日期：1993.12

  In the presence of 20 mol % of a chiral (acyloxy)borane (CAB) complex prepared from (2R,3R)-2-O-(2,6-diisopropoxybenzoyl)tartaric acid and borane-tetrahydrofuran, various allyltrimethylsilanes react with achiral aldehydes to afford the corresponding homoallylic alcohols in good yields with high diastereo- and enantioselectivities. Furthermore, the reactivity of allylation can be improved without reducing the enantioselelctivity by using 10-20 mol % of the CAB complex prepared from 3,5-bis(trifluoromethyl)phenylboronic acid and chiral tartaric acid derivative. The observed selectivities and re-face attack of nucleophiles on the carbonyl carbons of aldehydes imply that the extended transition-state model is applicable.