摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

(E,E)-3,7-Dimethyl-9-(tetrahydropyran-2'-yloxy)-2,7-nonadiene 1-cyanide | 157167-80-1

中文名称
——
中文别名
——
英文名称
(E,E)-3,7-Dimethyl-9-(tetrahydropyran-2'-yloxy)-2,7-nonadiene 1-cyanide
英文别名
(3E,8E)-4,8-dimethyl-10-(oxan-2-yloxy)deca-3,8-dienenitrile
(E,E)-3,7-Dimethyl-9-(tetrahydropyran-2'-yloxy)-2,7-nonadiene 1-cyanide化学式
CAS
157167-80-1
化学式
C17H27NO2
mdl
——
分子量
277.407
InChiKey
LCJCHJHTXOPYBK-XGGJEREUSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    427.3±45.0 °C(predicted)
  • 密度:
    0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    4.1
  • 重原子数:
    20
  • 可旋转键数:
    8
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.71
  • 拓扑面积:
    42.2
  • 氢给体数:
    0
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Stereospecific Synthesis of Suspensolide, a Male-Produced Pheromone of the Caribbean Fruit Fly, Anastrepha suspensa (Loew), and the Mexican Fruit Fly, Anastrepha ludens (Loew)
    摘要:
    An efficient synthesis of (E,E)-4,8-dimethyl-3,8-decadien-10-olide, suspensolide, a major component of the pheromone blend of the Caribbean and Mexican fruit flies, is described. The synthesis involves dicarboalumination of 1,6-heptadiyne with in situ conversion to a dialanate and reaction with paraformaldehyde. Monoprotection of the symmetrical diol formed in this process as the mono-THP derivative allowed conversion of the free hydroxyl to the chloride (NCS/DMS). Addition of one carbon to the chain was achieved by displacement of the chloride by cyanide (phase-transfer conditions) or the lithium salt of a thioorthoester. Hydrolysis of the masked carbonyls and deprotection of the omega-hydroxyl gave (E,E)-4,8-dimethyl-10-hydroxy-3,8-decadienoic acid. This diunsaturated hydroxy acid was cyclized to suspensolide in 30% yield using Mitsunobu conditions. The overall yield of suspensolide in this eight-step synthesis was 10%.
    DOI:
    10.1021/jo00096a029
  • 作为产物:
    参考文献:
    名称:
    Stereospecific Synthesis of Suspensolide, a Male-Produced Pheromone of the Caribbean Fruit Fly, Anastrepha suspensa (Loew), and the Mexican Fruit Fly, Anastrepha ludens (Loew)
    摘要:
    An efficient synthesis of (E,E)-4,8-dimethyl-3,8-decadien-10-olide, suspensolide, a major component of the pheromone blend of the Caribbean and Mexican fruit flies, is described. The synthesis involves dicarboalumination of 1,6-heptadiyne with in situ conversion to a dialanate and reaction with paraformaldehyde. Monoprotection of the symmetrical diol formed in this process as the mono-THP derivative allowed conversion of the free hydroxyl to the chloride (NCS/DMS). Addition of one carbon to the chain was achieved by displacement of the chloride by cyanide (phase-transfer conditions) or the lithium salt of a thioorthoester. Hydrolysis of the masked carbonyls and deprotection of the omega-hydroxyl gave (E,E)-4,8-dimethyl-10-hydroxy-3,8-decadienoic acid. This diunsaturated hydroxy acid was cyclized to suspensolide in 30% yield using Mitsunobu conditions. The overall yield of suspensolide in this eight-step synthesis was 10%.
    DOI:
    10.1021/jo00096a029
点击查看最新优质反应信息

文献信息

  • Stereospecific Synthesis of Suspensolide, a Male-Produced Pheromone of the Caribbean Fruit Fly, Anastrepha suspensa (Loew), and the Mexican Fruit Fly, Anastrepha ludens (Loew)
    作者:Ginna Hidalgo-Del Vecchio、Allan C. Oehlschlager
    DOI:10.1021/jo00096a029
    日期:1994.8
    An efficient synthesis of (E,E)-4,8-dimethyl-3,8-decadien-10-olide, suspensolide, a major component of the pheromone blend of the Caribbean and Mexican fruit flies, is described. The synthesis involves dicarboalumination of 1,6-heptadiyne with in situ conversion to a dialanate and reaction with paraformaldehyde. Monoprotection of the symmetrical diol formed in this process as the mono-THP derivative allowed conversion of the free hydroxyl to the chloride (NCS/DMS). Addition of one carbon to the chain was achieved by displacement of the chloride by cyanide (phase-transfer conditions) or the lithium salt of a thioorthoester. Hydrolysis of the masked carbonyls and deprotection of the omega-hydroxyl gave (E,E)-4,8-dimethyl-10-hydroxy-3,8-decadienoic acid. This diunsaturated hydroxy acid was cyclized to suspensolide in 30% yield using Mitsunobu conditions. The overall yield of suspensolide in this eight-step synthesis was 10%.
查看更多

同类化合物

(3S,4R)-3-氟四氢-2H-吡喃-4-胺 鲁比前列素中间体 顺-4-(四氢吡喃-2-氧)-2-丁烯-1-醇 顺-3-Boc-氨基-四氢吡喃-4-羧酸 锡烷,三丁基[3-[(四氢-2H-吡喃-2-基)氧代]-1-炔丙基]- 蒜味伞醇B 蒜味伞醇A 茉莉吡喃 苄基2,3-二-O-乙酰基-4-脱氧-4-C-硝基亚甲基-β-D-阿拉伯吡喃果糖苷 膜质菊内酯 红没药醇氧化物A 科立内酯 甲磺酸酯-四聚乙二醇-四氢吡喃醚 甲基[(噁烷-3-基)甲基]胺 甲基6-氧杂双环[3.1.0]己烷-2-羧酸酯 甲基4-脱氧吡喃己糖苷 甲基2,4,6-三脱氧-2,4-二-C-甲基吡喃葡己糖苷 甲基1,2-环戊烯环氧物 甲基-[2-吡咯烷-1-基-1-(四氢-吡喃-4-基)-乙基]-胺 甲基-(四氢吡喃-4-甲基)胺 甲基-(四氢吡喃-2-甲基)胺盐酸盐 甲基-(四氢吡喃-2-甲基)胺 甲基-(四氢-吡喃-3-基-胺 甲基-(四氢-吡喃-3-基)-胺盐酸盐 甲基-(4-吡咯烷-1-甲基四氢吡喃-4-基)-胺 甲基(5R)-3,4-二脱氧-4-氟-5-甲基-alpha-D-赤式-吡喃戊糖苷 环氧乙烷-2-醇乙酸酯 环己酮,6-[(丁基硫代)亚甲基]-2,2-二甲基-3-[(四氢-2H-吡喃-2-基)氧代]-,(3S)- 环丙基-(四氢-吡喃-4-基)-胺 玫瑰醚 独一味素B 溴-六聚乙二醇-四氢吡喃醚 氯菊素 氯丹环氧化物 氨甲酸,[[(四氢-2H-吡喃-2-基)氧代]甲基]-,乙基酯 氧化氯丹 正-(四氢-4-苯基-2h-吡喃-4-基)乙酰胺 次甲霉素 A 桉叶油醇 抗-11-氧杂三环[4.3.1.12,5]十一碳-3-烯-10-酮 戊二酸二甲酯 恩洛铂 异丙基-(四氢吡喃-4-基)胺 四氢吡喃醚-二聚乙二醇 四氢吡喃酮 四氢吡喃-4-醇 四氢吡喃-4-肼二盐酸盐 四氢吡喃-4-羧酸甲酯 四氢吡喃-4-羧酸噻吩酯