(S)-2-ethenyl-2,6-dimethylhept-5-en-1-ol | 485385-65-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-2-ethenyl-2,6-dimethylhept-5-en-1-ol
• 英文别名: (2S)-2-ethenyl-2,6-dimethylhept-5-en-1-ol
• CAS: 485385-65-7
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: DREYBWCZMNKFAO-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-ethenyl-2,6-dimethylhept-5-en-1-ol 在 吡啶 、 potassium tert-butylate 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 7.25h， 生成 bakuchiol methyl ether
  参考文献：
  名称：

  A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol and ent-Bakuchiol

  摘要：

  A facile asymmetric synthesis of Delta(3)-2-Hydroxybakuchiol, Bakuchiol, and ent-Bakuchiol is described through one common intermediate bearing a chiral all-carbon quaternary carbon center, which involves stereoselectively unconjugated alkylation of the alpha,beta-unsaturated imide bearing Evans' auxiliary, Takai-Utimoto reaction, Negishi reaction, and Heck reaction as key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.064
• 作为产物：
  描述：

  (E)-2-甲基-2-丁烯酰氯 在 咪唑 、 iron(III) chloride 、 锂硼氢 、 正丁基锂 、 四溴化碳 、 四甲基乙二胺 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 (S)-2-ethenyl-2,6-dimethylhept-5-en-1-ol
  参考文献：
  名称：

  A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol and ent-Bakuchiol

  摘要：

  A facile asymmetric synthesis of Delta(3)-2-Hydroxybakuchiol, Bakuchiol, and ent-Bakuchiol is described through one common intermediate bearing a chiral all-carbon quaternary carbon center, which involves stereoselectively unconjugated alkylation of the alpha,beta-unsaturated imide bearing Evans' auxiliary, Takai-Utimoto reaction, Negishi reaction, and Heck reaction as key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.064

文献信息

• Stereoselective Synthesis of the Tricyclic Core of (−)-Callophycoic Acid A
  作者：Akihiro Sakama、Rika Kameshima、Yuko Motohashi、Wataru Sumida、Yuta Unno、Keisuke Yoshida、Akihiro Ogura、Ken-ichi Takao

  DOI：10.1021/acs.joc.9b03114

  日期：2020.3.6

  Two stereocontrolled routes to the tricyclic core of (-)-callophycoic acid A are described. Our synthetic strategy relied on stereoselective allylboration using a new allylboronate reagent to construct the all-carbon quaternary stereocenter in the core, followed by efficient radical cyclization or palladium-catalyzed reductive cyclization to form its multisubstituted cyclohexane ring. The tetrahydrooxepin

  描述了到（-）-苯甲酸A的三环核心的两个立体控制的路线。我们的合成策略依赖于立体选择性烯丙基硼化，使用一种新的烯丙基硼酸酯试剂在核心中构建全碳四元立体中心，然后进行有效的自由基环化或钯催化的还原环化，以形成其多取代的环己烷环。通过分子内醚化构建四氢氧杂环戊烯环。这项研究提供了第一种方法来立体选择性地合成愈伤组织酸的特征性三环骨架。
• Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes: synthesis of a fragment of (+)-vibsanin A
  作者：Akihiro Sakama、Yoshiyasu Nishimura、Yuko Motohashi、Keisuke Yoshida、Ken-ichi Takao

  DOI：10.1016/j.tet.2016.07.030

  日期：2016.9

  Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes is described. Sugar-derived aldehydes were allylated with geranylboronate or nerylboronate to provide γ-adducts possessing quaternary stereocenters with high diastereoselectivity. The reaction was applied to the synthesis of a fragment of (+)-vibsanin A.

  描述了通过手性醛的烯丙基硼化的全碳四元立体中心的立体选择性构造。糖衍生的醛与香叶基硼酸酯或神经基硼酸酯烯丙基化，以提供具有高非对映选择性的具有季立体中心的γ加合物。该反应被用于合成（+）-vibsanin A的片段。
• Stereoselective Total Synthesis of Natural (S)-Bakuchiol and Its Enantiomer
  作者：Xiao-Long Du、Hong-Li Chen、Hui-Jin Feng、Yuan-Chao Li

  DOI：10.1002/hlca.200890041

  日期：2008.2

  A practical stereoselective synthesis of (S)-bakuchiol (1) and its enantiomer is reported. The important intermediate, (R)-configured β-siloxy aldehyde 5, was obtained in three steps from the easily available material geraniol (2) via the key step of Yamamoto's rearrangement of epoxy silyl ethers. (S)-Bakuchiol (1) and its enantiomer, (R)-bakuchiol (17), were finally obtained in different synthetic

  报道了一种实用的立体选择性合成（S）-幕果酚（1）及其对映异构体。通过山本重整环氧甲硅烷基醚的关键步骤，从容易获得的原料香叶醇（2）分三步获得了重要的中间体（R）构型的β-甲硅烷基醛5。最终以不同的合成顺序获得了香叶醇（2）的（S）-幕府酚（1）及其对映异构体（R）-幕府酚（17），总产率为51％（十步）和40％（九步）。， 分别。
• Stereoselective Pinacol-Type Rearrangement of 2,3-Epoxy Alcohols with Retention of Configuration Mediated by Bis(iodozincio)methane
  作者：Seijiro Matsubara、Hiromasa Yamamoto、Koichiro Oshima

  DOI：10.1002/1521-3773(20020802)41:15<2837::aid-anie2837>3.0.co;2-x

  日期：2002.8.2
• Construction of All-Carbon Quaternary Stereocenters by Zinc-Mediated Barbier-Type Allylation in Aqueous Media
  作者：Ken-ichi Takao、Kin-ichi Tadano、Tomo Miyashita、Nozomi Akiyama、Takuya Kurisu、Kohei Tsunoda

  DOI：10.3987/com-12-s(n)31

  日期：——

  Stereoselective construction of an all-carbon quaternary stereocenter by Barbier-type allylation in aqueous media is described. Sugar-derived aldehydes, 2,3-O-isopropylidene-D-glyceraldehyde and 2,4-O-benzylidene-D-threose, were reacted with geranyl chloride in the presence of zinc powder to provide gamma-adducts bearing quaternary stereocenters with good stereoselectivity.