(2S)-1-benzyloxyhept-6-en-2-ol | 207864-56-0

• 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: (2S)-1-benzyloxyhept-6-en-2-ol
• 英文别名: (S)-(+)-1-(benzyloxy)hept-6-en-2-ol；(2S)-1-phenylmethoxyhept-6-en-2-ol
• CAS: 207864-56-0
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: VUYFDZAPGZGNSW-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-1-benzyloxyhept-6-en-2-ol 在 lithium aluminium tetrahydride 、 Zn(N3)2-2 pyr 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 邻二氯苯 、 甲苯 为溶剂， 反应 6.0h， 生成 (2R,6R)-2-methyl-6-(phenylmethoxymethyl)piperidine
  参考文献：
  名称：

  Studies Directed Towards the Total Synthesis of (+)-Himbacine

  摘要：

  A convergent strategy towards himbacine (1), involving a Julia coupling between aldehyde 5 and sulfone 6 was found to be ineffective. The aldehyde 5 was synthesized via the thermal intramolecular cycloaddition of 4 with preferred formation of the endo-adduct. The Diels-Alder precursor 4 was obtained from butenolide 7, the result of a single-step condensation between the enoate derived from the (Z)-conjugated olefin 12 and 2-acetoxypropanal. In the context of the synthesis of sulfone 6 Taber's method for the synthesis of 2,6-trans-disubstituted piperidine was adapted towards a large scale synthesis of 49, a useful intermediate for the synthesis in this area.

  DOI：

  10.1055/s-1998-5928
• 作为产物：
  描述：

  4-溴-1-丁烯 、 (S)-苄氧甲基环氧乙烷 在 lithium tetrachlorocuprate 、 magnesium 作用下， 生成 (2S)-1-benzyloxyhept-6-en-2-ol
  参考文献：
  名称：

  Studies Directed Towards the Total Synthesis of (+)-Himbacine

  摘要：

  A convergent strategy towards himbacine (1), involving a Julia coupling between aldehyde 5 and sulfone 6 was found to be ineffective. The aldehyde 5 was synthesized via the thermal intramolecular cycloaddition of 4 with preferred formation of the endo-adduct. The Diels-Alder precursor 4 was obtained from butenolide 7, the result of a single-step condensation between the enoate derived from the (Z)-conjugated olefin 12 and 2-acetoxypropanal. In the context of the synthesis of sulfone 6 Taber's method for the synthesis of 2,6-trans-disubstituted piperidine was adapted towards a large scale synthesis of 49, a useful intermediate for the synthesis in this area.

  DOI：

  10.1055/s-1998-5928

文献信息

• Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of <i>P</i>-Stereogenic, <i>Z</i>-Configured Bicyclo[7.3.1]- and Bicyclo[8.3.1]phosphates
  作者：Jana L. Markley、Soma Maitra、Paul R. Hanson

  DOI：10.1021/acs.joc.5b02473

  日期：2016.2.5

  A phosphate tether-mediated ring-closing metathesis (RCM) study to the synthesis of Z-configured, P-stereogenic bicyclo[7.3.1]- and bicyclo[8.3.1]phosphates is reported. Investigations suggest that C3-substitution, olefin substitution, and proximity of the forming olefin to the bridgehead carbon of the bicyclic affect the efficiency and stereochemical outcome of the RCM event. This study demonstrates

  报道了磷酸酯系链介导的闭环复分解（RCM）研究合成Z-构型，P-立体异构的双环[7.3.1]-和双环[8.3.1]磷酸酯。研究表明，C3的取代，烯烃的取代以及形成的烯烃与双环桥头碳的接近度会影响RCM事件的效率和立体化学结果。这项研究证明了磷酸酯系链介导的C 2对称，含1,3-抗二醇的二烯的不对称化在具有潜在的合成和生物学用途的大环磷酸酯的产生中的效用。
• Phosphate tether-mediated ring-closing metathesis for the generation of medium to large, P-stereogenic bicyclo[n.3.1]phosphates
  作者：Soma Maitra、Jana L. Markley、Rambabu Chegondi、Paul R. Hanson

  DOI：10.1016/j.tet.2015.06.016

  日期：2015.9

  A phosphate tether-mediated ring-closing metathesis study towards the synthesis of P-stereogenic bicyclo[6.3.1]-, bicyclo[7.3.1]-, and bicyclo[8.3.1]phosphates is reported. This study demonstrates expanded utility of phosphate tether-mediated desymmetrization of C2-symmetric, 1,3-anti-diol dienes in generating complex medium to large, P-stereogenic bicyclo[n.3.1]phosphates.

  报道了磷酸酯系链介导的闭环复分解研究，其合成P-立体异构双环[6.3.1]-，双环[7.3.1]-和双环[8.3.1]磷酸。这项研究表明，磷酸酯系链介导的C 2对称的1,3-抗二醇二烯脱对称作用在产生大到P立体异构双环[n.3.1]磷酸盐的复杂介质中具有扩展的效用。
• 10.1021/acs.orglett.4c01969
  作者：Alexandridis, Anestis、Rancon, Thibault、Halliday, Abigail、Kochem, Amélie、Quintard, Adrien

  DOI：10.1021/acs.orglett.4c01969

  日期：——

  newly formed stereocenters. When iron-catalyzed borrowing hydrogen from allylic alcohols was combined with a stereocontrolled organocatalytic oxa-Michael addition, a wide array of chiral tetrahydropyrans were efficiently prepared. The reaction could be performed in a diastereoselective manner from pre-existing stereocenters or enantioselectively from achiral substrates. The key to success was the reactivity

  立体控制的 oxa-Michael 加成具有挑战性，因为该过程具有高度可逆性，最终导致新形成的立体中心外消旋化。当铁催化的烯丙醇借氢与立体控制的有机催化氧杂迈克尔加成相结合时，可以有效地制备多种手性四氢吡喃。该反应可以以非对映选择性方式从预先存在的立体中心进行或以对映选择性方式从非手性底物进行。成功的关键是铁络合物的反应活性，它对烯丙醇脱氢具有选择性，并不可逆地导致反应生成最终产物。
• Studies Directed Towards the Total Synthesis of (+)-Himbacine
  作者：Sven Hofman

  DOI：10.1055/s-1998-5928

  日期：1998.3

  A convergent strategy towards himbacine (1), involving a Julia coupling between aldehyde 5 and sulfone 6 was found to be ineffective. The aldehyde 5 was synthesized via the thermal intramolecular cycloaddition of 4 with preferred formation of the endo-adduct. The Diels-Alder precursor 4 was obtained from butenolide 7, the result of a single-step condensation between the enoate derived from the (Z)-conjugated olefin 12 and 2-acetoxypropanal. In the context of the synthesis of sulfone 6 Taber's method for the synthesis of 2,6-trans-disubstituted piperidine was adapted towards a large scale synthesis of 49, a useful intermediate for the synthesis in this area.
• Investigation of Pd(II)-Catalyzed Cyclization of Chiral θ-Hydroxy-α,β,γ,δ-unsaturated Dienol
  作者：Jun'ichi Uenishi、Akiko Ida、Naoyuki Hoshiya

  DOI：10.3987/com-14-s(k)77

  日期：——

  PdCl2(MeCN)(2) catalyzed intramolecular cyclization of optically pure theta-hydroxyl-alpha,beta,gamma,delta-dienylethanols 1 and 2 are described. cis and trans-2-Benzyloxymethyl-6-(1,3-pentadienyl)tetrahydropyrans 3 and 4 were produced stereoselectively with a ratio of 3:1 in excellent yield. No 1,5-chirality transfer was observed in the cyclization reaction.