(Z)-8-phenyloct-4-en-1-ol | 345961-04-8

• 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: (Z)-8-phenyloct-4-en-1-ol
• CAS: 345961-04-8
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: CPCSNAXFCXASSW-UPHRSURJSA-N

物化性质

• 沸点：
  331.7±21.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (Z)-8-phenyloct-4-en-1-ol 在 1‐methyl‐2‐azaadamantane‐N‐oxyl 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane–Iodine Catalytic System

  摘要：

  A novel catalytic system using I-2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.

  DOI：

  10.1021/acs.orglett.5b01797
• 作为产物：
  描述：

  4-苯丁酸甲酯 在 六甲基磷酰三胺 、 正丁基锂 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 11.33h， 生成 (Z)-8-phenyloct-4-en-1-ol
  参考文献：
  名称：

  Catalytic Enantioselective Iodocyclization of γ-Hydroxy-cis-alkenes

  摘要：

  Enantioselective iodocyclization of gamma-hydroxy-cis-alkenes has been achieved using I2 in the presence of an unprecedented catalyst system generated from (R,R)-t-Bu-salen-Co(II) complex and NCS to produce 2-monosubstituted tetrahydrofurans up to 90% ee. While NCS turned out to be the essential additive, neither (R,R)-salen-Co(II) nor (R,R)-salen-Co(III) by itself is likely to be the active species responsible for the asymmetric intramolecular iodoetherification.

  DOI：

  10.1021/ja0369921

文献信息

• Asymmetric Iodocyclization Catalyzed by Salen–CrIIICl: Its Synthetic Application to Swainsonine
  作者：Hyo Young Kwon、Chul Min Park、Sung Bae Lee、Joo-Hack Youn、Sung Ho Kang

  DOI：10.1002/chem.200701199

  日期：2008.1.18

  The previously developed enantioselective iodocyclization of gamma-hydroxy-cis-alkenes required 30 mol% of (R,R)-salen-Co(II) complex as chiral catalyst and 0.75 equivalent of N-chlorosuccinimide (NCS) as activator to produce 2-substituted tetrahydrofurans with 61 to 90% ee. Due to the considerable loading amount of the Co(II) complex, another more effective catalyst was pursued by screening (R,R)-salen-transition

  先前开发的γ-羟基-顺式烯烃的对映选择性碘环化需要30摩尔％的（R，R）-salen-Co（II）配合物作为手性催化剂和0.75当量的N-氯代琥珀酰亚胺（NCS）作为活化剂以生产2- ee为61至90％的取代四氢呋喃。由于Co（II）配合物的大量负载，通过筛选（R，R）-salen-过渡金属配合物寻求了另一种更有效的催化剂。当10摩尔％的催化剂应用0.5当量的NCS时，相应的Cr（III）Cl（84％ee），Mn（II）Cl（52％ee）和Co（II ）配合物（66％ee）。条件的完善建立了一种新的催化对映选择性碘环化方案，该方案使用碘在7摩尔％的被0活化的（R，R）-salen-Cr（III）Cl络合物存在下进行。
• Controlled Semihydrogenation of Aminoalkynes Using Ethylenediamine as a Poison of Lindlar's Catalyst
  作者：Kevin R. Campos、Dongwei Cai、Michel Journet、Jason J. Kowal、Robert D. Larsen、Paul J. Reider

  DOI：10.1021/jo015514a

  日期：2001.5.1
• Catalytic Enantioselective Iodocyclization of γ-Hydroxy-<i>cis</i>-alkenes
  作者：Sung Ho Kang、Sung Bae Lee、Chul Min Park

  DOI：10.1021/ja0369921

  日期：2003.12.1

  Enantioselective iodocyclization of gamma-hydroxy-cis-alkenes has been achieved using I2 in the presence of an unprecedented catalyst system generated from (R,R)-t-Bu-salen-Co(II) complex and NCS to produce 2-monosubstituted tetrahydrofurans up to 90% ee. While NCS turned out to be the essential additive, neither (R,R)-salen-Co(II) nor (R,R)-salen-Co(III) by itself is likely to be the active species responsible for the asymmetric intramolecular iodoetherification.
• Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane–Iodine Catalytic System
  作者：Shoji Fujita、Masanori Abe、Masatoshi Shibuya、Yoshihiko Yamamoto

  DOI：10.1021/acs.orglett.5b01797

  日期：2015.8.7

  A novel catalytic system using I-2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.