(Z)-11-(Tetrahydro-pyran-2-yloxy)-undec-2-en-1-ol | 87242-05-5

• 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)-11-(Tetrahydro-pyran-2-yloxy)-undec-2-en-1-ol
• 英文别名: (Z)-11-(oxan-2-yloxy)undec-2-en-1-ol
• CAS: 87242-05-5
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: HTGJZAGCNCCAGL-TWGQIWQCSA-N

物化性质

• 沸点：
  397.5±42.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  19.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-11-(Tetrahydro-pyran-2-yloxy)-undec-2-en-1-ol 在 吡啶 、 manganese(IV) oxide 、 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 (E,E)-9,11-十四碳二烯-1-醇乙酸酯
  参考文献：
  名称：

  Olefinic acetates, Δ-9,11–14: OAc and Δ-7,9–12: OAc used as sex pheromone components in three geometrid moths,Idaea aversata, I. straminata, andI. biselata (Geometridae, Lepidoptera)

  摘要：

  Pheromone compounds so far identified from most geometrid moths consist of all-Z diene, triene, or tetraene hydrocarbons with chain lengths of C-17 to C-21, and their monoepoxide derivatives biosynthesized from linoleic and linolenic acids. The present study reports the occurrence of olefinic acetates as sex pheromones in three species of Geometridae. (Z,Z)-9,11-tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate found in female gland extracts of Idaea aversata elicited significant responses from conspecific male antennae in gas chromatography with electroantennographic detection (GC-EAD). In extracts of I. straminata, (Z,E)-7,9-dodecadienyl acetate, (E,Z)-7,9-dodecadienyl acetate, and (Z,Z)-7,9-dodecadienyl acetate were found, and the synthetic compounds elicited strong responses from conspecific male antennae. In the third species, I. biselata, only (Z,Z)-7,9-dodecadienyl acetate was found in the female extracts, and this compound elicited a strong EAD response from the conspecific male antenna. The identities of the pheromone components in I. aversata and I. straminata were further confirmed according to their characteristic ions after GC-MS analyses. Single sensillum recordings from I. aversata showed two types of pheromone-detecting sensilla present on the male antenna. One type contained two receptor neurons, one of which was specifically tuned to (Z,Z)-9,11-tetradecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. A second type contained one neuron responding to (Z,Z)-7,9-dodecadienyl acetate. The two types were clearly different also with respect to external morphology, the former being considerably longer and having a larger base diameter. Also in I. straminata two physiological types of sensilla could be distinguished. One type contained two neurons, one of which responded to (Z,Z)-7,9-dodecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. The second type contained one neuron, responding to (Z,Z)-7,9-dodecadienyl acetate. No correlation between external morphology and physiological response of the investigated sensilla was observed in I. straminata. In field tests, a two-component blend containing (Z,Z)-9,11-tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate in a ratio of 10:1 was attractive to males of I. aversata. This two-component blend was also attractive to males of I. straminata, but in a ratio of 1:1. High numbers of male I. biselata were caught in traps baited with (Z,Z)-7,9-dodecadienyl acetate alone. The incorporation of deuterium labels into pheromone components after topical application of deuterium-labeled palmitic acid confirmed that the pheromone components of I. aversata could be synthesized from this precursor, as has been previously observed for acetate pheromone components of many other moth species. Our results suggest that an evolutionary reversal back to the production of palmitic acid-derived pheromone components has occurred within the geometrid subfamily Sterrhinae.

  DOI：

  10.1007/bf02027728
• 作为产物：
  描述：

  1,8-辛二醇 在 Lindlar's catalyst 正丁基锂 、 氢气 作用下， 以 喹啉 、 正己烷 、 氯仿 为溶剂， 反应 2.0h， 生成 (Z)-11-(Tetrahydro-pyran-2-yloxy)-undec-2-en-1-ol
  参考文献：
  名称：

  Ochiai, Masahito; Ukita, Tatsuzo; Fujita, Eiichi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 5, p. 1641 - 1645

  摘要：

  DOI：

文献信息

• Chattopadhyay, A.; Mamdapur, V. R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 868 - 869
  作者：Chattopadhyay, A.、Mamdapur, V. R.

  DOI：——

  日期：——
• CHATTOPADHYAY, A.;MAMDAPUR, V. R., INDIAN J. CHEM., 26,(1987) N 9, 868-869
  作者：CHATTOPADHYAY, A.、MAMDAPUR, V. R.

  DOI：——

  日期：——