(1R,2R,3S,5S)-(+)-neoisopinocampheol | 2734-31-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,3S,5S)-(+)-neoisopinocampheol
• 英文别名: (1R,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol
• CAS: 2734-31-8
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: REPVLJRCJUVQFA-XAVMHZPKSA-N

物化性质

• 熔点：
  45-47 °C
• 沸点：
  217.0±0.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906199090

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,5S)-(+)-neoisopinocampheol 在 sodium dichromate 作用下， 生成 [1R-(1alpha,2beta,5alpha)]-2,6,6-三甲基双环[3.1.1]庚烷-3-酮
  参考文献：
  名称：

  用烟草培养细胞对单环和双环单萜类化合物进行生物转化的对映选择性

  摘要：

  研究了对薄荷烷和双环 [2.2.1] 和 [3.1.1] 庚烷衍生物的对映体对与烟草培养细胞的生物转化。发现(i)培养的细胞区分对-薄荷醇-2-醇和双环[2.2.1]庚烷-2-醇和双环[3.1.1]庚烷-3-醇衍生物的对映异构体，并对映选择性转化将这些醇转化为相应的酮，(ii) 细胞高度还原 p-menthan-2-one 衍生物的羰基，但不还原 p-menthan-3-ones 的羰基，以及 (iii) 细胞区分双环[3.1.1]hept-2-en-4-one（verbenone）的对映异构体，并对映选择性还原（1S，5S）-对映异构体的C-C双键。

  DOI：

  10.1246/bcsj.61.869
• 作为产物：
  描述：

  [1R-(1alpha,2beta,5alpha)]-2,6,6-三甲基双环[3.1.1]庚烷-3-酮 在 sodium tetrahydroborate 作用下， 生成 (1R,2R,3S,5S)-(+)-neoisopinocampheol
  参考文献：
  名称：

  用烟草培养细胞对单环和双环单萜类化合物进行生物转化的对映选择性

  摘要：

  研究了对薄荷烷和双环 [2.2.1] 和 [3.1.1] 庚烷衍生物的对映体对与烟草培养细胞的生物转化。发现(i)培养的细胞区分对-薄荷醇-2-醇和双环[2.2.1]庚烷-2-醇和双环[3.1.1]庚烷-3-醇衍生物的对映异构体，并对映选择性转化将这些醇转化为相应的酮，(ii) 细胞高度还原 p-menthan-2-one 衍生物的羰基，但不还原 p-menthan-3-ones 的羰基，以及 (iii) 细胞区分双环[3.1.1]hept-2-en-4-one（verbenone）的对映异构体，并对映选择性还原（1S，5S）-对映异构体的C-C双键。

  DOI：

  10.1246/bcsj.61.869

文献信息

• Enantioselectivity in the Biotransformation of Bicyclo[3.1.1]heptanes with the Cultured Cells of<i>Nicotiana tabacum</i>
  作者：Takayuki Suga、Hiroki Hamada、Toshifumi Hirata

  DOI：10.1246/cl.1987.471

  日期：1987.3.5

  The biotransformation of the enantiomeric pairs of bicyclo[3.1.1]heptane derivatives with the cultured cells of Nicotiana tabacum was investigated. The hydrogenation of the C–C double bond of verbenone took place enantioselectively in preference of the (1S,5S)-enantiomer and the hydrogen attack occurred stereospecifically from the re-face at its C-2. The oxidation of the hydroxyl group of neoisopinocampheol

  研究了双环[3.1.1]庚烷衍生物对映体对与烟草培养细胞的生物转化。马鞭草的 C-C 双键的氢化优先于 (1S,5S)-对映异构体发生对映选择性，氢攻击从其 C-2 的背面立体特异性地发生。新异松香酚羟基的氧化优先发生在 (1S,2S,3R,5R)-对映异构体中，而这种对映选择性氧化不是新异松醇的情况。
• Schmidt, Chemische Berichte, 1947, vol. 80, p. 533,537
  作者：Schmidt

  DOI：——

  日期：——
• Calcium Intake and Bone Mass Development Among Israeli Adolescent Girls
  作者：Geila S. Rozen、Gad Rennert、Hedy S. Rennert、Gissel Diab、Dib Daud、Sofia Ish-Shalom

  DOI：10.1080/07315724.2001.10719035

  日期：2001.6

  Objective: To determine the possible relationship between food and life style habits and bone health in adolescent Israeli females.Methods: 2,000 adolescent Israeli Jewish and Arab high-school girls (mean age 14.5) completed a semi-quantitative food frequency questionnaire and a personal history questionnaire. 27 food components were calculated fur each subject. Bone mineral content and density were determined for 112 subjects with calcium intake below 800 mg/day.Results: Average calcium intake was found to be 1,260 mg/day, but 20% of all girls had a calcium intake below 800 mg/day. All low-energy diets were very low in calcium, as mean calcium intake per 1,000 calories was 411 +/- 128 grams. A large percentage of diets with less than 800 mg calcium were also deficient in phosphorus (95.2%), magnesium (84.8%), iron (90.5%) and zinc (100%). Due to differences in food sources, Jewish girls had more phosphorus in their diet, but less magnesium and iron compared to Arab girls. Calcium and zinc deficiencies in Jewish and Arab diets were similar. A negative correlation was found between body mass index (BMI) and age at menarche for all girls in the study. Bone mineral density (BMD) measured for girls with calcium intake below 800 mg/day distributed normally around the average when compared to age matched controls despite their low calcium intake. There was a strong positive correlation between BMD and bone mineral content (BMC) at all sites and body weights.Conclusions: Low calcium intake, other nutritional deficiencies and delayed menarche due to low-energy diet in the growing period and in adolescence may prevent the formation of healthy bones. There is no evidence of lower bone mass among the low calcium intake group in the study population at this stage. It remains to be documented if the window of opportunity for optimal bone accretion for this group will be missed in the future, possibly lending to increased risk of osteoporosis.
• Schmidt, Bericht von Schimmel and Co., p. 79,83
  作者：Schmidt

  DOI：——

  日期：——
• Schmidt, Chemische Berichte, 1944, vol. 77/79, p. 544,549
  作者：Schmidt

  DOI：——

  日期：——