(Z)-4-iodo-1-(tetrahydro-2H-2-pyranyloxy)but-3-ene | 109872-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (Z)-4-iodo-1-(tetrahydro-2H-2-pyranyloxy)but-3-ene
• 英文别名: 1-Iodo-4-(tetrahydropyranyloxy)-1(Z)-butene；2-[(Z)-4-iodobut-3-enoxy]oxane
• CAS: 109872-90-4
• 化学式: C₉H₁₅IO₂
• 分子量: 282.121
• InChiKey: VGELMEXJQDKWFI-KXFIGUGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴氟甲基膦酸二乙酯 、 (Z)-4-iodo-1-(tetrahydro-2H-2-pyranyloxy)but-3-ene 在 copper(I) bromide 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 以93%的产率得到diethyl [(Z)-1,1-difluoro-5-(tetrahydro-2H-2-pyranyloxy)-2-pentenyl]phosphonate
  参考文献：
  名称：

  Synthesis of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids and the related methano analogues. Remarkable effect of the nucleobases and the cyclopropane rings on inhibitory activity toward purine nucleoside phosphorylase

  摘要：

  A series of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids, (E)-2a,b and (Z)-2a,b, as well as the related methano analogues (+/-)-3a,b and (+/-)-4a,b were prepared for evaluation of their PNP inhibitory activities. The cyclopopane ring and the hypoxanthine residue were found to increase the profile of inhibitory activity. The IC50 and K-i values of difluoro({1R*,2S*)-2-[2-(6-oxo-6,9-dihydro-1H-9-purinyl)ethyl]cyclopropyl)methylphosphonic acid (+/-)3b toward PNP purified from Cellulomonas sp. were determined to be 70 nM and 8.8 nM, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)80023-0
• 作为产物：
  描述：

  1-Iodo-4-(tetrahydropyranyloxy)-1-butyne 生成 (Z)-4-iodo-1-(tetrahydro-2H-2-pyranyloxy)but-3-ene
  参考文献：
  名称：

  Stereoselective Synthesis of 1,4-Dienes. Application to the Preparation of Insect Pheromones (3Z,6Z)-Dodeca-3,6-dien-1-ol and (4E,7Z)-Trideca-4,7-dienyl Acetate

  摘要：

  Stereoselective synthesis of Z,E and Z,Z-1,4-dienes has been achieved by the cross-coupling of allylic substrates with vinyl organometallic reagents. Key to this strategy was the development of a method for regiospecific incorporation of a tri-n-butylstannyl group in the gamma-position of the allylic cross-coupling partner. The steric bulk of this moiety ensures the stereochemical integrity of the allylic double bond throughout the coupling sequence and is easily replaced by hydrogen in the coupled product. This strategy has been applied to the synthesis of the termite trail marker pheromone 22 and the leafminer moth sex pheromone 28.

  DOI：

  10.1021/jo00119a043

文献信息

• Synthesis of 2,2-difluoroesters by iododifluoroacetate-copper with organic halides
  作者：Takeo Taguchi、Osamu Kitagawa、Tsutomu Morikawa、Tohru Nishiwaki、Hideya Uehara、Hatsumi Endo、Yoshiro Kobayashi

  DOI：10.1016/s0040-4039(00)85409-x

  日期：1986.1
• Palladium-catalyzed intermolecular vinylation of cyclic alkenes
  作者：Richard C. Larock、William H. Gong

  DOI：10.1021/jo00270a011

  日期：1989.4
• TAGUCHI TAKEO; KITAGAWA OSAMU; MORIKAWA TSUTOMU; NISHIWAKI TOHRU; UEHARA +, TETRAHEDRON LETT., 27,(1986) N 50, 6103-6106
  作者：TAGUCHI TAKEO、 KITAGAWA OSAMU、 MORIKAWA TSUTOMU、 NISHIWAKI TOHRU、 UEHARA +

  DOI：——

  日期：——
• Synthesis of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids and the related methano analogues. Remarkable effect of the nucleobases and the cyclopropane rings on inhibitory activity toward purine nucleoside phosphorylase
  作者：Tsutomu Yokomatsu、Hiroshi Abe、Mutsumi Sato、Kenji Suemune、Taro Kihara、Shinji Soeda、Hiroshi Shimeno、Shiroshi Shibuya

  DOI：10.1016/s0968-0896(98)80023-0

  日期：1998.12

  A series of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids, (E)-2a,b and (Z)-2a,b, as well as the related methano analogues (+/-)-3a,b and (+/-)-4a,b were prepared for evaluation of their PNP inhibitory activities. The cyclopopane ring and the hypoxanthine residue were found to increase the profile of inhibitory activity. The IC50 and K-i values of difluoro(1R*,2S*)-2-[2-(6-oxo-6,9-dihydro-1H-9-purinyl)ethyl]cyclopropyl)methylphosphonic acid (+/-)3b toward PNP purified from Cellulomonas sp. were determined to be 70 nM and 8.8 nM, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereoselective Synthesis of 1,4-Dienes. Application to the Preparation of Insect Pheromones (3Z,6Z)-Dodeca-3,6-dien-1-ol and (4E,7Z)-Trideca-4,7-dienyl Acetate
  作者：Michael W. Hutzinger、Allan C. Oehlschlager

  DOI：10.1021/jo00119a043

  日期：1995.7

  Stereoselective synthesis of Z,E and Z,Z-1,4-dienes has been achieved by the cross-coupling of allylic substrates with vinyl organometallic reagents. Key to this strategy was the development of a method for regiospecific incorporation of a tri-n-butylstannyl group in the gamma-position of the allylic cross-coupling partner. The steric bulk of this moiety ensures the stereochemical integrity of the allylic double bond throughout the coupling sequence and is easily replaced by hydrogen in the coupled product. This strategy has been applied to the synthesis of the termite trail marker pheromone 22 and the leafminer moth sex pheromone 28.