3-phenylmethyl-pent-4-yn-1-ol | 226993-01-7

• 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: 3-phenylmethyl-pent-4-yn-1-ol
• 英文别名: 3-Benzylpent-4-yn-1-ol
• CAS: 226993-01-7
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: CMFOFAKMWVZXJK-UHFFFAOYSA-N

物化性质

• 沸点：
  301.8±30.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-phenylmethyl-pent-4-yn-1-ol 在 三乙胺 、 二异丙胺 、 copper(I) bromide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 34.0h， 生成
  参考文献：
  名称：

  Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters

  摘要：

  A unique method to affect intramolecular aminooxygenation and dioxygenation of allenols and allenylsulfonamides is described. These operationally simple reactions occur under neutral or basic conditions where copper(II) carboxylates serve as reaction promoter, oxidant, and carboxylate source. Moderate to high yields of heterocycle-functionalized vinyl carboxylate esters are formed with moderate to high levels of diastereoselectivity. Such vinyl carboxylate esters could serve as precursors to alpha-amino and alpha-oxy ketones and derivatives thereof.

  DOI：

  10.1021/acs.orglett.5b02833
• 作为产物：
  描述：

  溴甲苯 在 正丁基锂 、 二异丁基氢化铝 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 生成 3-phenylmethyl-pent-4-yn-1-ol
  参考文献：
  名称：

  Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters

  摘要：

  A unique method to affect intramolecular aminooxygenation and dioxygenation of allenols and allenylsulfonamides is described. These operationally simple reactions occur under neutral or basic conditions where copper(II) carboxylates serve as reaction promoter, oxidant, and carboxylate source. Moderate to high yields of heterocycle-functionalized vinyl carboxylate esters are formed with moderate to high levels of diastereoselectivity. Such vinyl carboxylate esters could serve as precursors to alpha-amino and alpha-oxy ketones and derivatives thereof.

  DOI：

  10.1021/acs.orglett.5b02833

文献信息

• Copper-Catalyzed Cyclization/aza-Claisen Rearrangement Cascade Initiated by Ketenimine Formation: An Efficient Stereocontrolled Synthesis of α-Allyl Cyclic Amidines
  作者：Hua-Dong Xu、Zhi-Hong Jia、Ke Xu、Mei Han、Sai-Nan Jiang、Jing Cao、Jia-Cheng Wang、Mei-Hua Shen

  DOI：10.1002/anie.201405331

  日期：2014.8.25

  and convenient synthesis of α‐allyl cyclic amidines has been achieved by applying a novel cascade reaction. Copper(I)‐mediated in situ N‐sulfonyl ketenimine formation from the reaction of a terminal alkyne with sulfonyl azide is followed by an intramolecular nucleophilic attack on the central carbon atom by an allylic tertiary amine, and then an aza‐Claisen rearrangement takes place through a chair

  通过应用新型的级联反应，可以高效，方便地合成α-烯丙基环状am。末端炔烃与磺酰叠氮化物反应生成的铜（I）介导的原位N-磺酰基酮亚胺形成，随后是烯丙基叔胺对中心碳原子的分子内亲核攻击，然后发生氮杂-克莱森重排通过椅子过渡态为标题的am提供完全的立体控制。
• Cobalt-mediated cycloisomerization of δ-substituted ε-acetylenic β-ketoesters construction of angular triquinane by a sequence ene/Pauson-Khand reactions
  作者：Jean-Luc Renaud、Corinne Aubert、Max Malacria

  DOI：10.1016/s0040-4020(99)00172-6

  日期：1999.4

  The preparation of δ-substituted ε-acetylenic β-ketoesters is fully described. Their cobalt-mediated Conia-ene reactions led to variously functionalized methylenecyclopentanes in high yields and with a moderate control of the 1,4 diastereoselectivity. A sequence involving the cobalt-mediated ene and Pauson-Khand reactions is presented and allowed the construction of the angular triquinane framework

  充分描述了δ-取代的ε-炔属β-酮酸酯的制备。他们的钴介导的Conia-ene反应以高收率产生了各种官能化的亚甲基环戊烷，并适度控制了1,4非对映选择性。提出了涉及钴介导的烯和Pauson-Khand反应的序列，并允许构建角三喹烷骨架。
• Multicyclic compounds for use as melanin concentrating hormone antagonists in the treatment of obesity and diabetes
  申请人：Ammenn Jochen

  公开号：US20050272718A1

  公开（公告）日：2005-12-08

  The present invention relates to a melanin concentrating hormone antagonist compound of formula I: (I); or a pharmaceutically acceptable salt, solvate, enantiomer or prodrug thereof useful in the treatment, prevention or amelioration of symptoms associated with obesity and related diseases.

  本发明涉及一种式 I 的黑色素浓缩激素拮抗剂化合物：(I)；或其药学上可接受的盐、溶液剂、对映体或原药，可用于治疗、预防或改善与肥胖及相关疾病有关的症状。
• Gold-Catalyzed Diastereoselective Cycloisomerization of Alkylidene-Cyclopropane-Bearing 1,6-Diynes
  作者：Hongchao Zheng、Laura L. Adduci、Ryan J. Felix、Michel R. Gagné

  DOI：10.1002/anie.201405147

  日期：2014.7.21

  AbstractAn unprecedented gold‐catalyzed diastereoselective cycloisomerization of 1,6‐diynes bearing an alkylidene cyclopropane moiety has been developed. This methodology enables rapid access to a variety of 1,2‐trimethylenenorbornanes, which are important building blocks in the preparations of abiotic and sesquiterpene core structures.
• MULTICYCLIC COMPOUNDS FOR USE AS MELANIN CONCENTRATING HORMONE ANTAGONISTS IN THE TREATMENT OF OBESITY AND DIABETES
  申请人：ELI LILLY AND COMPANY

  公开号：EP1505968A1

  公开（公告）日：2005-02-16