6-phenylhexa-4,5-dien-1-ol | 173439-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-phenylhexa-4,5-dien-1-ol
• 英文别名: 6-phenyl-4,5-hexadienol
• CAS: 173439-52-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: QRDHZJALLXEOQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  6-phenylhexa-4,5-dien-1-ol 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 N-6-phenyl-4,5-hexadienyl-p-toluene sulfonamide
  参考文献：
  名称：

  Acylation-cyclization of allenes

  摘要：

  Allenes bearing a nucleophilic group cyclize on treatment with acyltetracarbonyl cobalt complexes in the presence of mild bases. Various nucleophilic groups and cobalt complexes can be used to give highly functionalized pyrrolidines, cyclopentanes and tetrahydrofurans. Disubstituted allenes may be used in the reaction. 1,3-disubstituted allenes give products with high stereoselectivity.

  DOI：

  10.1016/0040-4020(95)00816-q
• 作为产物：
  描述：

  5-(2-Ethoxy-ethoxy)-pent-1-yne 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 56.0h， 生成 6-phenylhexa-4,5-dien-1-ol
  参考文献：
  名称：

  Acylation-cyclization of allenes

  摘要：

  Allenes bearing a nucleophilic group cyclize on treatment with acyltetracarbonyl cobalt complexes in the presence of mild bases. Various nucleophilic groups and cobalt complexes can be used to give highly functionalized pyrrolidines, cyclopentanes and tetrahydrofurans. Disubstituted allenes may be used in the reaction. 1,3-disubstituted allenes give products with high stereoselectivity.

  DOI：

  10.1016/0040-4020(95)00816-q

文献信息

• Nickel-Catalyzed Asymmetric Hydrocyanation of Allenes
  作者：Jinguo Long、Jihui Gao、Xianjie Fang

  DOI：10.1021/acs.orglett.9b03938

  日期：2020.1.17

  The first catalytic enantioselective hydrocyanation of allenes catalyzed by a (R,R)-Ph-BPE-Ni(0) complex catalyst has been accomplished. Numerous optically active allylic nitriles were obtained in good yield with excellent enantioselectivities (up to 98% ee).

  由（R，R）-Ph-BPE-Ni（0）络合物催化剂催化的丙二烯的第一催化对映选择性氢氰化反应已经完成。以良好的收率和优异的对映选择性（高达98％ee）获得了许多旋光性烯丙基腈。
• Stereoselective Synthesis of Chiral Polycyclic Indolic Architectures through Pd⁰-Catalyzed Tandem Deprotection/Cyclization of Tetrahydro-β-carbolines on Allenes
  作者：Valérian Gobé、Xavier Guinchard

  DOI：10.1002/chem.201500273

  日期：2015.6.1

  Enantioenriched N‐allyl tetrahydro‐β‐carbolines were prepared by chiral phosphoric acid‐catalyzed Pictet–Spengler reactions. The compounds undergo Pd0‐catalyzed cyclizations through a tandem deprotection/cyclization process. The regioselectivity of the attack is controlled by the chain length and by the substitution pattern of the allene function. Products resulting from 5‐exo‐ or 6‐exo‐attack were obtained

  通过手性磷酸催化的Pictet-Spengler反应制备了对映体富集的N-烯丙基四氢-β-咔啉。这些化合物通过串联的脱保护/环化过程经历Pd 0催化的环化。攻击的区域选择性由链长和丙二烯官能团的取代模式控制。从5 exo-或6 exo-攻击获得的产物的非对映异构体比例高达95：5。Azepinopyrrido [3,4 b ]吲哚通过7-获得内切-cyclizations。
• Construction of Monocyclic Eight-Membered Rings: Intermolecular Rhodium(I)-Catalyzed [6+2] Cycloaddition of 4-Allenals with Alkynes
  作者：Yoshihiro Oonishi、Akihito Hosotani、Yoshihiro Sato

  DOI：10.1002/anie.201206508

  日期：2012.11.12

  Rounding up: A RhI‐catalyzed intermolecular cycloaddition of 4‐allenals with alkynes has been developed that provides various monocyclic eight‐membered rings in good to high yields in a stereoselective manner (see scheme). In addition, the chirality of the starting allene is transferred in this reaction, thereby giving optically active monocyclic eight‐membered ring compounds.

  舍入：一个铑我催化的4- allenals与炔烃环加成间已经开发了提供以立体选择性的方式以良好至高产率各种单环八元环（参见方案）。另外，起始丙二烯的手性在该反应中转移，从而得到光学活性的单环八元环化合物。
• Intramolecular Nucleophilic Acyl Substitution Reaction of 3,4-Alkadienyl Carbonates Mediated by Ti(O-<i>i</i>-Pr)₄/2 <i>i</i>-PrMgCl Reagent. Efficient Synthesis of Optically Active β,γ-Unsaturated Esters with an α-Substituent
  作者：Yukio Yoshida、Sentaro Okamoto、Fumie Sato

  DOI：10.1021/jo961401t

  日期：1996.1.1

  readily generated by the reaction of Ti(O-i-Pr)(4) with 2 i-PrMgCl, resulted in an intramolecular nucleophilic acyl substitution (INAS) reaction to afford vinyltitanium compounds 3 which, in turn, reacted with H(3)O(+), D(2)O, or iodine to give alpha-substituted beta,gamma-unsaturated esters 4 in good to excellent yields. The olefin moiety of the hydrolysis product 4 has (Z)-geometry mainly except for

  用低价钛试剂二异丙氧基（eta（2）-丙烯）钛（1）处理3,4-链二烯基碳酸酯2a-i，该反应很容易通过Ti（Oi-Pr）（4）与2i反应生成-PrMgCl导致分子内亲核酰基取代（INAS）反应，得到乙烯基钛化合物3，后者再与H（3）O（+），D（2）O或碘反应生成α-取代的β， γ-不饱和酯4的收率为好至极好。水解产物4的烯烃部分主要具有（Z）几何形状，除了4h以外。从手性2f或2g开始，反应立体定向进行，得到仅具有（Z）-烯烃几何结构的旋光的α-取代的β，γ-不饱和酯4f或4g。
• Synthesis of Multifunctionalized Furans from Diazoallenes: Rearrangement of 6-Methylenebicyclo[3.1.0]hexanes
  作者：Richmond Sarpong、Tuanli Yao、Allen Hong

  DOI：10.1055/s-2006-950215

  日期：2006.11

  The synthesis of annulated tetrasubstituted furans using diazoallene precursors is described. This reaction provides efficient access to synthetically useful furan intermediates, which are other- wise difficult to obtain.

  描述了使用重氮烯前体合成环化四取代呋喃。该反应提供了合成有用的呋喃中间体的有效途径，否则这些中间体很难获得。