(+)-2-O-acetyl-5-ketoborneol | 73650-99-4

• 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: (+)-2-O-acetyl-5-ketoborneol
• 英文别名: 5-oxo-d-bornyl acetate；(1R)-6endo-acetoxy-bornan-3-one；(1R)-6endo-Acetoxy-bornan-3-on；[(1R,2S,4R)-1,7,7-trimethyl-5-oxo-2-bicyclo[2.2.1]heptanyl] acetate
• CAS: 73650-99-4
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: LJJDMLPORNJBCT-PEXQALLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-2-O-acetyl-5-ketoborneol 在 sodium methylate 、 silver carbonate 作用下， 以 甲醇 、 苯 为溶剂， 反应 7.0h， 生成 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(1R,2S,4R)-1,7,7-trimethyl-5-oxo-2-bicyclo[2.2.1]heptanyl]oxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  姜中的Stomachic原理。三，一种抗溃疡药，由6-生姜磺酸和三种原产于台湾的姜黄的单酰基二乳糖基甘油酯A，B和C制成。

  摘要：

  从台湾种植的生姜的干根茎姜黄中分离出抗溃疡成分6-姜磺酸和三种单酰基二乳糖基甘油A，B和C姜糖脂，以及（+）-Angelicoidenol- 2-O-β-D-吡喃葡萄糖苷。基于化学反应和物理化学证据，已经确定了6-姜磺酸，姜糖脂A，B和C的结构。另外，基于其从d-冰片的合成，阐明了（+）-Angelioidenenol-2-O-β-D-吡喃葡萄糖苷的绝对立体结构。6-氨基磺酸的辛辣性较6-姜醇和6-寿果酚弱，且抗溃疡作用更强。

  DOI：

  10.1248/cpb.42.1226
• 作为产物：
  描述：

  (+)-冰片 在 吡啶 、 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 14.0h， 生成 (+)-2-O-acetyl-5-ketoborneol
  参考文献：
  名称：

  姜中的Stomachic原理。三，一种抗溃疡药，由6-生姜磺酸和三种原产于台湾的姜黄的单酰基二乳糖基甘油酯A，B和C制成。

  摘要：

  从台湾种植的生姜的干根茎姜黄中分离出抗溃疡成分6-姜磺酸和三种单酰基二乳糖基甘油A，B和C姜糖脂，以及（+）-Angelicoidenol- 2-O-β-D-吡喃葡萄糖苷。基于化学反应和物理化学证据，已经确定了6-姜磺酸，姜糖脂A，B和C的结构。另外，基于其从d-冰片的合成，阐明了（+）-Angelioidenenol-2-O-β-D-吡喃葡萄糖苷的绝对立体结构。6-氨基磺酸的辛辣性较6-姜醇和6-寿果酚弱，且抗溃疡作用更强。

  DOI：

  10.1248/cpb.42.1226

文献信息

• Enantiospecific Synthesis of Both Enantiomers of the Longtailed Mealybug Pheromone and Their Evaluation in a New Zealand Vineyard
  作者：Remya Ramesh、Vaughn Bell、Andrew M. Twidle、Rajesh Gonnade、D. Srinivasa Reddy

  DOI：10.1021/acs.joc.5b01131

  日期：2015.8.7

  from the corresponding bornyl acetates. The use of readily accessible chiral starting materials and lactone–lactone rearrangement are the highlights of the present synthesis. The biological activities of the two enantiomers and racemic mixture were tested in a New Zealand vineyard. The (S)-(+)-enantiomer was significantly more attractive to P. longispinus males than the racemic mixture or the (R)-(−)-enantiomer

  由相应的乙酸乙酸烯丙酯制备长假单胞菌的不规则单萜类性信息素及其对映体。使用容易获得的手性起始原料和内酯-内酯重排是本合成的重点。在新西兰的葡萄园中测试了两种对映异构体和外消旋混合物的生物活性。（S）-（+）-对映异构体比外消旋混合物或（R）-（-）-对映异构体对长柄假单胞菌雄性更具吸引力。
• Shibuya, Hirotaka; Fujioka, Hiromichi; Kajiwara, Akiharu, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 4, p. 1271 - 1279
  作者：Shibuya, Hirotaka、Fujioka, Hiromichi、Kajiwara, Akiharu、Yamamoto, Yoshio、Kitagawa, Isao

  DOI：——

  日期：——
• Sahashi et al., Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1934, vol. 25, p. 47,52,56,59,60
  作者：Sahashi et al.

  DOI：——

  日期：——
• Interlaminar fracture and low-velocity impact of carbon/epoxy composite materials
  作者：J. H. Hwang、O. Kwon、C. S. Lee、W. Hwang

  DOI：10.1007/bf02681828

  日期：2000.3

  The interlaminar fracture and the low-velocity impact behavior of carbon/epoxy composite materials have been studied using width-tapered double cantilever beam (WTDCB), end-notched flexure (ENF), and Boeing impact specimens. The objectives of this research are to determine the essential parameters governing interlaminar-fracture and damage of realistic laminated composites and to characterize a correlation between the critical strain energy release rates measured by interlaminar fracture and by low-velocity impact tests. The geometry and the lay-tip sequence of specimens are designed to probe various conditions such as the skewness parameter, beam volume, and test fixture. The effect of interfacial ply orientations and crack propagation directions on interlaminar fracture toughness and the effect of ply orientations and thickness on impact behavior ar-e examined. The critical strain energy release rare was calculated from the respective tests: in the interlaminar fracture test the compliance method and linear beam theory are used; the residual energy calculated from the impact test and the total delamination area estimated by ultrasonic inspection are used ill the low-velocity, impact test. Results show that the critical strain energy release rate is affected mainly by ply orientations. The critical strain energy release rate measured by the low-velocity impact test lies between the mode I and mode II critical strain energy release rates obtained by the interlaminar fracture test.
• Takeuchi; Sahashi, Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1933, vol. 22, p. 59,63
  作者：Takeuchi、Sahashi

  DOI：——

  日期：——